Num_Atoms_Murcko Num_BridgeBonds_Murcko Reactant Product Scale(mmol) Yield year Primary_Author canonical_smiles_reactant Smiles Num_Atoms Num_BridgeBonds canonical_smiles_product Reactant_c Product_c Canonical_Smiles_Murcko_reactant Canonical_Smiles_Murcko_Product murcko_Name_Reactant murcko_Name_Product MP Chiral 13 0 9 9a 12.8 94 2011 MacMillan CC(C)(C)OC(=O)N1CCc2c(C1)[nH]c3ccccc23 CC(C)(C)OC(=O)N1CCc2c(C1)[nH]c3ccccc23 20 0 COc1ccc(Cn2c3CN(CCc3c4ccccc24)C(=O)OC(C)(C)C)cc1 9.MacMillan 9a.MacMillan C1CCC2C(C1)NC3CNCCC23 C1CCC2C(C1)NC3CNCCC23 MacMillanC1CCC2C(C1)NC3CNCCC23 MacMillanC1CCC2C(C1)NC3CNCCC23 13 0 9a 9b 1.55 87 2011 MacMillan COc1ccc(Cn2c3CN(CCc3c4ccccc24)C(=O)OC(C)(C)C)cc1 COc1ccc(Cn2c3CN(CCc3c4ccccc24)C(=O)OC(C)(C)C)cc1 29 0 COc1ccc(Cn2c(C=O)c(CCNC(=O)OC(C)(C)C)c3ccccc23)cc1 9a.MacMillan 9b.MacMillan C1CCC2C(C1)NC3CNCCC23 C1CCC2NCCC2C1 MacMillanC1CCC2C(C1)NC3CNCCC23 MacMillanC1CCC2NCCC2C1 ND 9 0 9b 10 12.24 81 2011 MacMillan COc1ccc(Cn2c(C=O)c(CCNC(=O)OC(C)(C)C)c3ccccc23)cc1 COc1ccc(Cn2c(C=O)c(CCNC(=O)OC(C)(C)C)c3ccccc23)cc1 30 0 COc1ccc(Cn2c(\C=C\[Se]C)c(CCNC(=O)OC(C)(C)C)c3ccccc23)cc1 9b.MacMillan 10.MacMillan C1CCC2NCCC2C1 C1CCC2NCCC2C1 MacMillanC1CCC2NCCC2C1 MacMillanC1CCC2NCCC2C1 ND 9 0 10 11 0.6 82 2011 MacMillan COc1ccc(Cn2c(\C=C\[Se]C)c(CCNC(=O)OC(C)(C)C)c3ccccc23)cc1 COc1ccc(Cn2c(\C=C\[Se]C)c(CCNC(=O)OC(C)(C)C)c3ccccc23)cc1 32 0 COc1ccc(CN2C3=CC=C(C=O)[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)cc1 10.MacMillan 11.MacMillan C1CCC2NCCC2C1 C1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2NCCC2C1 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 ND 16 0 11 11a 4.12 86 2011 MacMillan COc1ccc(CN2C3=CC=C(C=O)[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)cc1 COc1ccc(CN2C3=CC=C(C=O)[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)cc1 34 0 COc1ccc(CN2C3=CC=C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)cc1 11.MacMillan 11a.MacMillan C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 ND yes 16 0 11a 11b 0.79 88 2011 MacMillan COc1ccc(CN2C3=CC=C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)cc1 COc1ccc(CN2C3=CC=C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)cc1 32 0 COC(=O)C1=C2N(Cc3ccc(OC)cc3)c4ccccc4[C@@]25CCN([C@H]5C=C1)C(=O)OC(C)(C)C 11a.MacMillan 11b.MacMillan C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 ND yes 16 0 11b 12 0.24 81 2011 MacMillan COC(=O)C1=C2N(Cc3ccc(OC)cc3)c4ccccc4[C@@]25CCN([C@H]5C=C1)C(=O)OC(C)(C)C COC(=O)C1=C2N(Cc3ccc(OC)cc3)c4ccccc4[C@@]25CCN([C@H]5C=C1)C(=O)OC(C)(C)C 36 0 COC(=O)C1CC[C@@H]2NCC[C@]23[C@H]1N(Cc4ccc(OC)cc4)c5ccccc35 11b.MacMillan 12.MacMillan C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 ND yes 16 0 12 13a 0.288 84 2011 MacMillan COC(=O)C1CC[C@@H]2NCC[C@]23[C@H]1N(Cc4ccc(OC)cc4)c5ccccc35 COC(=O)C1CC[C@@H]2NCC[C@]23[C@H]1N(Cc4ccc(OC)cc4)c5ccccc35 29 0 COC(=O)C1=CC[C@@H]2N(C\C(=C\COC(=O)C)\I)CC[C@]23[C@H]1N(Cc4ccc(OC)cc4)c5ccccc35 12.MacMillan 13a.MacMillan C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 NA yes 16 0 13a 14 0.146 91 2011 MacMillan COC(=O)C1=CC[C@@H]2N(C\C(=C\COC(=O)C)\I)CC[C@]23[C@H]1N(Cc4ccc(OC)cc4)c5ccccc35 COC(=O)C1=CC[C@@H]2N(C\C(=C\COC(=O)C)\I)CC[C@]23[C@H]1N(Cc4ccc(OC)cc4)c5ccccc35 38 0 COc1ccc(CN2[C@H]3C(=CC[C@@H]4N(C\C(=C\CO)\I)CC[C@]34c5ccccc25)CO)cc1 13a.MacMillan 14.MacMillan C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 NA yes 16 0 14 15 0.3748 58 2011 MacMillan COc1ccc(CN2[C@H]3C(=CC[C@@H]4N(C\C(=C\CO)\I)CC[C@]34c5ccccc25)CO)cc1 COc1ccc(CN2[C@H]3C(=CC[C@@H]4N(C\C(=C\CO)\I)CC[C@]34c5ccccc25)CO)cc1 33 0 COc1ccc(CN2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27)cc1 14.MacMillan 15.MacMillan C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MacMillanC1CCC2C(C1)NC3CCCC4NCCC234 MacMillanC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 NA yes 22 18 15 16 0.0283 66 2011 MacMillan COc1ccc(CN2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27)cc1 COc1ccc(CN2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27)cc1 32 18 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 15.MacMillan 16.MacMillan C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MacMillanC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MacMillanC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ND yes 22 18 16 Strychnine 0.0526 69 2011 MacMillan OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 16.MacMillan Strychnine.MacMillan C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 MacMillanC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MacMillanC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 ND yes 24 25 Strychnine 2011 MacMillan O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.MacMillan C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 MacMillanC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . ND yes 9 0 Tryptophyl Bromide 9 71.2 100 2011 Vanderwal BrCCc1c[nH]c2ccccc12 BrCCc1c[nH]c2ccccc12 12 0 C=CCNCCc1c[nH]c2ccccc12 Tryptophyl Bromide.Vanderwal 9.Vanderwal C1CCC2NCCC2C1 C1CCC2NCCC2C1 VanderwalC1CCC2NCCC2C1 VanderwalC1CCC2NCCC2C1 9 0 9 11 71.5 38.6 2011 Vanderwal C=CCNCCc1c[nH]c2ccccc12 C=CCNCCc1c[nH]c2ccccc12 15 0 C=CCN(CCc1c[nH]c2ccccc12)\C=C\C=C\C=O 9.Vanderwal 11.Vanderwal C1CCC2NCCC2C1 C1CCC2NCCC2C1 VanderwalC1CCC2NCCC2C1 VanderwalC1CCC2NCCC2C1 NA 12 0 10 11 33.9 81 2011 Vanderwal [O-][N+](=O)c1ccc(c(c1)[N+](=O)[O-])[n+]2ccccc2 [O-][N+](=O)c1ccc(c(c1)[N+](=O)[O-])[n+]2ccccc2 18 0 C=CCN(CCc1c[nH]c2ccccc12)\C=C\C=C\C=O 10.Vanderwal 11.Vanderwal C1CCC(CC1)N2CCCCC2 C1CCC2NCCC2C1 VanderwalC1CCC(CC1)N2CCCCC2 VanderwalC1CCC2NCCC2C1 9 0 9 9 53 2011 Vanderwal C=CCNCCc1c[nH]c2ccccc12 C=CCNCCc1c[nH]c2ccccc12 15 0 C=CCNCCc1c[nH]c2ccccc12 9.Vanderwal 9.Vanderwal C1CCC2NCCC2C1 C1CCC2NCCC2C1 VanderwalC1CCC2NCCC2C1 VanderwalC1CCC2NCCC2C1 9 0 11 12 0.738 64 2011 Vanderwal C=CCN(CCc1c[nH]c2ccccc12)\C=C\C=C\C=O C=CCN(CCc1c[nH]c2ccccc12)\C=C\C=C\C=O 21 0 C=CCN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 11.Vanderwal 12.Vanderwal C1CCC2NCCC2C1 C1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2NCCC2C1 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 104-106 9 0 11 12 2.7 60 2011 Vanderwal C=CCN(CCc1c[nH]c2ccccc12)\C=C\C=C\C=O C=CCN(CCc1c[nH]c2ccccc12)\C=C\C=C\C=O 21 0 C=CCN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 11.Vanderwal 12.Vanderwal C1CCC2NCCC2C1 C1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2NCCC2C1 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 104-106 5 0 14 S1 2011 Vanderwal C[Si]1(C)OCC=C1CO C[Si]1(C)OCC=C1CO 9 0 C[Si]1(C)OCC=C1CBr 14.Vanderwal S1.Vanderwal C1CO[SiH2]C1 C1CO[SiH2]C1 VanderwalC1CO[SiH2]C1 VanderwalC1CO[SiH2]C1 5 0 S1 15 2011 Vanderwal C[Si]1(C)OCC=C1CBr C[Si]1(C)OCC=C1CBr 9 0 C[Si](C)(C)\C(=C/CO)\CBr S1.Vanderwal 15.Vanderwal C1CO[SiH2]C1 VanderwalC1CO[SiH2]C1 . 16 0 12 7 0.159 57 2011 Vanderwal C=CCN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 C=CCN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 21 0 O=CC1=CC[C@@H]2NCC[C@]23C1Nc4ccccc34 12.Vanderwal 7.Vanderwal C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 91-3 no 16 0 7 16 2011 Vanderwal O=CC1=CC[C@@H]2NCC[C@]23C1Nc4ccccc34 O=CC1=CC[C@@H]2NCC[C@]23C1Nc4ccccc34 18 0 C[Si](C)(C)\C(=C/CO)\CN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 7.Vanderwal 16.Vanderwal C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 12 16 0.999 69 2011 Vanderwal C=CCN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 C=CCN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 21 0 C[Si](C)(C)\C(=C/CO)\CN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 12.Vanderwal 16.Vanderwal C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 no 16 0 16 2 0.1 10 2011 Vanderwal C[Si](C)(C)\C(=C/CO)\CN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 C[Si](C)(C)\C(=C/CO)\CN1CC[C@@]23[C@@H]1CC=C(C=O)C2Nc4ccccc34 27 0 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 16.Vanderwal 2.Vanderwal C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 VanderwalC1CCC2C(C1)NC3CCCC4NCCC234 VanderwalC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 115-7 no 22 18 2 Strychnine 0.01 2011 Vanderwal OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 2.Vanderwal Strychnine.Vanderwal C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 VanderwalC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 VanderwalC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 ND no 24 25 Strychnine 2011 Vanderwal O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Vanderwal C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 VanderwalC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . no 9 0 Indole-3-carboxaldehyde 4 6.89 90 2010 Andrade O=Cc1c[nH]c2ccccc12 O=Cc1c[nH]c2ccccc12 11 0 C=CCC(NCc1ccccc1)c2c[nH]c3ccccc23 Indole-3-carboxaldehyde.Andrade 4.Andrade C1CCC2NCCC2C1 C1CCC2NCCC2C1 AndradeC1CCC2NCCC2C1 AndradeC1CCC2NCCC2C1 9 0 4 8 2.24 94 2010 Andrade C=CCC(NCc1ccccc1)c2c[nH]c3ccccc23 C=CCC(NCc1ccccc1)c2c[nH]c3ccccc23 21 0 BrCC(=O)N(Cc1ccccc1)C(CC=C)c2c[nH]c3ccccc23 4.Andrade 8.Andrade C1CCC2NCCC2C1 C1CCC2NCCC2C1 AndradeC1CCC2NCCC2C1 AndradeC1CCC2NCCC2C1 no 9 0 8 9 1.01 90 2010 Andrade BrCC(=O)N(Cc1ccccc1)C(CC=C)c2c[nH]c3ccccc23 BrCC(=O)N(Cc1ccccc1)C(CC=C)c2c[nH]c3ccccc23 25 0 COC(=O)\C=C\CC(N(Cc1ccccc1)C(=O)CBr)c2c[nH]c3ccccc23 8.Andrade 9.Andrade C1CCC2NCCC2C1 C1CCC2NCCC2C1 AndradeC1CCC2NCCC2C1 AndradeC1CCC2NCCC2C1 no 9 0 9 10 0.22 95 2010 Andrade COC(=O)\C=C\CC(N(Cc1ccccc1)C(=O)CBr)c2c[nH]c3ccccc23 COC(=O)\C=C\CC(N(Cc1ccccc1)C(=O)CBr)c2c[nH]c3ccccc23 29 0 COC(=O)\C=C\CC1N(Cc2ccccc2)C(=O)CC13C=Nc4ccccc34 9.Andrade 10.Andrade C1CCC2NCCC2C1 C1CCC2C(C1)NCC23CCNC3 AndradeC1CCC2NCCC2C1 AndradeC1CCC2C(C1)NCC23CCNC3 no 13 0 10 17 1.06 90 2010 Andrade COC(=O)\C=C\CC1N(Cc2ccccc2)C(=O)CC13C=Nc4ccccc34 COC(=O)\C=C\CC1N(Cc2ccccc2)C(=O)CC13C=Nc4ccccc34 28 0 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)C(=O)C[C@]24C1Nc5ccccc45 10.Andrade 17.Andrade C1CCC2C(C1)NCC23CCNC3 C1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NCC23CCNC3 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 no 16 0 17 18 7.02 81 2010 Andrade COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)C(=O)C[C@]24C1Nc5ccccc45 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)C(=O)C[C@]24C1Nc5ccccc45 28 0 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)C(=S)C[C@]24C1Nc5ccccc45 17.Andrade 18.Andrade C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 152-5 no 16 0 18 19 5.07 74 2010 Andrade COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)C(=S)C[C@]24C1Nc5ccccc45 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)C(=S)C[C@]24C1Nc5ccccc45 28 0 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1Nc5ccccc45 18.Andrade 19.Andrade C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 19 21 0.85 75 2010 Andrade COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1Nc5ccccc45 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1Nc5ccccc45 27 0 COC(=O)C1=CC[C@@H]2NCC[C@]23C1Nc4ccccc34 19.Andrade 21.Andrade C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 19 20 2010 Andrade COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1Nc5ccccc45 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1Nc5ccccc45 27 0 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1N(C(=O)OCCCl)c5ccccc45 19.Andrade 20.Andrade C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 no 16 0 20 21 2010 Andrade COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1N(C(=O)OCCCl)c5ccccc45 COC(=O)C1=CC[C@@H]2N(Cc3ccccc3)CC[C@]24C1N(C(=O)OCCCl)c5ccccc45 33 0 COC(=O)C1=CC[C@@H]2NCC[C@]23C1Nc4ccccc34 20.Andrade 21.Andrade C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 21 23 0.28 63 2010 Andrade COC(=O)C1=CC[C@@H]2NCC[C@]23C1Nc4ccccc34 COC(=O)C1=CC[C@@H]2NCC[C@]23C1Nc4ccccc34 20 0 COC(=O)C1=CC[C@@H]2N(C\C(=C\CO[Si](C)(C)C(C)(C)C)\I)CC[C@]23C1Nc4ccccc34 21.Andrade 23.Andrade C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 23 24 0.155 85 2010 Andrade COC(=O)C1=CC[C@@H]2N(C\C(=C\CO[Si](C)(C)C(C)(C)C)\I)CC[C@]23C1Nc4ccccc34 COC(=O)C1=CC[C@@H]2N(C\C(=C\CO[Si](C)(C)C(C)(C)C)\I)CC[C@]23C1Nc4ccccc34 33 0 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 23.Andrade 24.Andrade C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CCCC4NCCC234 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 NA no 18 13 24 25 0.133 80 2010 Andrade COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 32 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 24.Andrade 25.Andrade C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 NA no 18 13 24 24.1 2010 Andrade COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 32 13 COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO[Si](C)(C)C(C)(C)C 24.Andrade 24.1.Andrade C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 NA no 18 13 24.1 24.2 2010 Andrade COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO[Si](C)(C)C(C)(C)C COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO[Si](C)(C)C(C)(C)C 32 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO[Si](C)(C)C(C)(C)C 24.1.Andrade 24.2.Andrade C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 24.2 25 2010 Andrade COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO[Si](C)(C)C(C)(C)C COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO[Si](C)(C)C(C)(C)C 32 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 24.2.Andrade 25.Andrade C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 25 26 2010 Andrade COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO 25 13 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 25.Andrade 26.Andrade C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ND no 22 18 26 Strychnine 2010 Andrade OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1C4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 26.Andrade Strychnine.Andrade C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 AndradeC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 AndradeC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 ND no 18 13 25 Strychnine 0.106 49 2010 Andrade COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34C1Nc5ccccc45)C/C/2=C/CO 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25.Andrade Strychnine.Andrade C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 AndradeC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 AndradeC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 no 24 25 Strychnine 2010 Andrade O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Andrade C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 AndradeC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . ND no 9 0 26 22 1 68 2007 Padwa OC(=O)Cc1c[nH]c2ccccc12 OC(=O)Cc1c[nH]c2ccccc12 13 0 CC(C)(C)OC(=O)N(C(=O)Cc1c[nH]c2ccccc12)c3occc3 26.Padwa 22.Padwa C1CCC2NCCC2C1 C(CC1CNC2CCCCC12)NC3CCCO3 PadwaC1CCC2NCCC2C1 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 17 0 22 27 5.9 88 2007 Padwa CC(C)(C)OC(=O)N(C(=O)Cc1c[nH]c2ccccc12)c3occc3 CC(C)(C)OC(=O)N(C(=O)Cc1c[nH]c2ccccc12)c3occc3 25 0 CC(=O)n1cc(CC(=O)N(C(=O)OC(C)(C)C)c2occc2)c3ccccc13 22.Padwa 27.Padwa C(CC1CNC2CCCCC12)NC3CCCO3 C(CC1CNC2CCCCC12)NC3CCCO3 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 100-102 17 0 27 11 3.1 77 2007 Padwa CC(=O)n1cc(CC(=O)N(C(=O)OC(C)(C)C)c2occc2)c3ccccc13 CC(=O)n1cc(CC(=O)N(C(=O)OC(C)(C)C)c2occc2)c3ccccc13 28 0 CC(=O)n1cc(CC(=O)Nc2occc2)c3ccccc13 27.Padwa 11.Padwa C(CC1CNC2CCCCC12)NC3CCCO3 C(CC1CNC2CCCCC12)NC3CCCO3 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 102-103 17 0 11 18 20 61 2007 Padwa CC(=O)n1cc(CC(=O)Nc2occc2)c3ccccc13 CC(=O)n1cc(CC(=O)Nc2occc2)c3ccccc13 21 0 CC(=O)n1cc(CC(=O)N(Cc2ccccc2C)c3occc3)c4ccccc14 11.Padwa 18.Padwa C(CC1CNC2CCCCC12)NC3CCCO3 C(CC1CNC2CCCCC12)NC3CCCO3 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 164-5 17 0 18 19 0.8 95 2007 Padwa CC(=O)n1cc(CC(=O)N(Cc2ccccc2C)c3occc3)c4ccccc14 CC(=O)n1cc(CC(=O)N(Cc2ccccc2C)c3occc3)c4ccccc14 29 0 N1([C@@]2([C@]3(c4c1cccc4)C(=CCC2=O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C 18.Padwa 19.Padwa C(CC1CNC2CCCCC12)NC3CCCO3 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC(CC1CNC2CCCCC12)NC3CCCO3 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 96-97 16 0 19 20 2.6 65 2007 Padwa N1([C@@]2([C@]3(c4c1cccc4)C(=CCC2=O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C N1([C@@]2([C@]3(c4c1cccc4)C(=CCC2=O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C 29 0 Cc1ccccc1CN2CC[C@@]34[C@@H]2CC[C@H](O)C3Nc5ccccc45 19.Padwa 20.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 184-186 no 16 0 19 19.1 2007 Padwa N1([C@@]2([C@]3(c4c1cccc4)C(=CCC2=O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C N1([C@@]2([C@]3(c4c1cccc4)C(=CCC2=O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C 29 0 N1([C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C 19.Padwa 19.1.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 no 16 0 19.1 19.2 2007 Padwa N1([C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C N1([C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C(=O)C3)Cc1c(cccc1)C)[H])C(=O)C 29 0 N1[C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C(=O)C3)Cc1c(cccc1)C)[H] 19.1.Padwa 19.2.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 19.2 19.3 2007 Padwa N1[C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C(=O)C3)Cc1c(cccc1)C)[H] N1[C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C(=O)C3)Cc1c(cccc1)C)[H] 26 0 N1[C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C=C3)Cc1c(cccc1)C)[H] 19.2.Padwa 19.3.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 19.3 20 2007 Padwa N1[C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C=C3)Cc1c(cccc1)C)[H] N1[C@@]2([C@]3(c4c1cccc4)C(=CC[C@@H]2O)N(C=C3)Cc1c(cccc1)C)[H] 25 0 Cc1ccccc1CN2CC[C@@]34[C@@H]2CC[C@H](O)C3Nc5ccccc45 19.3.Padwa 20.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 20 36 0.3 68 2007 Padwa Cc1ccccc1CN2CC[C@@]34[C@@H]2CC[C@H](O)C3Nc5ccccc45 Cc1ccccc1CN2CC[C@@]34[C@@H]2CC[C@H](O)C3Nc5ccccc45 25 0 O[C@H]1CC[C@@H]2NCC[C@]23[C@H]1Nc4ccccc34 20.Padwa 36.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 36 37 0.54 80 2007 Padwa O[C@H]1CC[C@@H]2NCC[C@]23[C@H]1Nc4ccccc34 O[C@H]1CC[C@@H]2NCC[C@]23[C@H]1Nc4ccccc34 17 0 COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC[C@H](O)[C@@H]2Nc4ccccc34 36.Padwa 37.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 37 37NN 0.11 86 2007 Padwa COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC[C@H](O)[C@@H]2Nc4ccccc34 COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC[C@H](O)[C@@H]2Nc4ccccc34 26 0 COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC[C@H](O)[C@@H]2N(Cc4ccc(OC)cc4OC)c5ccccc35 37.Padwa 37NN.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 37NN 34 1.5 80 2007 Padwa COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC[C@H](O)[C@@H]2N(Cc4ccc(OC)cc4OC)c5ccccc35 COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC[C@H](O)[C@@H]2N(Cc4ccc(OC)cc4OC)c5ccccc35 37 0 COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CCC(=O)C2N(Cc4ccc(OC)cc4OC)c5ccccc35 37NN.Padwa 34.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 NA no 16 0 34 38 0.57 56 2007 Padwa COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CCC(=O)C2N(Cc4ccc(OC)cc4OC)c5ccccc35 COCOC\C=C(/I)\CN1CC[C@@]23[C@@H]1CCC(=O)C2N(Cc4ccc(OC)cc4OC)c5ccccc35 37 0 COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C(=O)C3N(Cc5ccc(OC)cc5OC)c6ccccc46 34.Padwa 38.Padwa C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 PadwaC1CCC2C(C1)NC3CCCC4NCCC234 PadwaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 NA no 18 13 38 35 0.29 72 2007 Padwa COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C(=O)C3N(Cc5ccc(OC)cc5OC)c6ccccc46 COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C(=O)C3N(Cc5ccc(OC)cc5OC)c6ccccc46 36 13 COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1\C(=C/OC)\C3N(Cc5ccc(OC)cc5OC)c6ccccc46 38.Padwa 35.Padwa C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 PadwaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 PadwaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 NA no 18 13 35 33 2007 Padwa COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1\C(=C/OC)\C3N(Cc5ccc(OC)cc5OC)c6ccccc46 COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1\C(=C/OC)\C3N(Cc5ccc(OC)cc5OC)c6ccccc46 38 13 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 35.Padwa 33.Padwa C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 PadwaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 PadwaC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 NA no 22 18 33 Strychnine 2007 Padwa OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1C4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 33.Padwa Strychnine.Padwa C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 PadwaC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 PadwaC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 NA no 18 13 35 Strychnine 0.015 43 2007 Padwa COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1\C(=C/OC)\C3N(Cc5ccc(OC)cc5OC)c6ccccc46 COCOC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1\C(=C/OC)\C3N(Cc5ccc(OC)cc5OC)c6ccccc46 38 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 35.Padwa Strychnine.Padwa C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 PadwaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 PadwaC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 no 24 25 Strychnine 2007 Padwa O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2C5N1c7ccccc67 25 25 Strychnine.Padwa C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 PadwaC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . 278-283 no 10 0 19 20 50 56 2004 Fukuyama c1ccc2ncccc2c1 c1ccc2ncccc2c1 10 0 OC\C=C/c1ccccc1N=C=S 19.Fukuyama 20.Fukuyama C1CCC2NCCCC2C1 C1CCCCC1 FukuyamaC1CCC2NCCCC2C1 Fukuyama_C1CCCCC1 6 0 20 21 13.1 98 2004 Fukuyama OC\C=C/c1ccccc1N=C=S OC\C=C/c1ccccc1N=C=S 13 0 CC(C)(C)[Si](C)(C)OC\C=C/c1ccccc1N=C=S 20.Fukuyama 21.Fukuyama C1CCCCC1 C1CCCCC1 Fukuyama_C1CCCCC1 Fukuyama_C1CCCCC1 NA 6 0 21 22 12.5 71 2004 Fukuyama CC(C)(C)[Si](C)(C)OC\C=C/c1ccccc1N=C=S CC(C)(C)[Si](C)(C)OC\C=C/c1ccccc1N=C=S 20 0 COC(=O)C(C(=O)OC)C(=S)Nc1ccccc1\C=C/CO[Si](C)(C)C(C)(C)C 21.Fukuyama 22.Fukuyama C1CCCCC1 C1CCCCC1 Fukuyama_C1CCCCC1 Fukuyama_C1CCCCC1 NA 6 0 22 4 2.56 52 2004 Fukuyama COC(=O)C(C(=O)OC)C(=S)Nc1ccccc1\C=C/CO[Si](C)(C)C(C)(C)C COC(=O)C(C(=O)OC)C(=S)Nc1ccccc1\C=C/CO[Si](C)(C)C(C)(C)C 29 0 COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCO[Si](C)(C)C(C)(C)C 22.Fukuyama 4.Fukuyama C1CCCCC1 C1CCC2NCCC2C1 Fukuyama_C1CCCCC1 FukuyamaC1CCC2NCCC2C1 NA 6 0 6 8 328 62 2004 Fukuyama OC(=O)c1ccccc1 OC(=O)c1ccccc1 9 0 COC(=O)C1=CCC[C@H](Br)[C@H]1O 6.Fukuyama 8.Fukuyama C1CCCCC1 C1CCCCC1 FukuyamaC1CCCCC1 FukuyamaC1CCCCC1 6 0 8 9 49.8 46 2004 Fukuyama COC(=O)C1=CCC[C@H](Br)[C@H]1O COC(=O)C1=CCC[C@H](Br)[C@H]1O 12 0 COC(=O)C1=CCC[C@H](Br)[C@H]1O 8.Fukuyama 9.Fukuyama C1CCCCC1 C1CCCCC1 FukuyamaC1CCCCC1 FukuyamaC1CCCCC1 NA no 6 0 9 10 23 73 2004 Fukuyama COC(=O)C1=CCC[C@H](Br)[C@H]1O COC(=O)C1=CCC[C@H](Br)[C@H]1O 12 0 OCC1=CCC[C@H](Br)[C@H]1O 9.Fukuyama 10.Fukuyama C1CCCCC1 C1CCCCC1 FukuyamaC1CCCCC1 FukuyamaC1CCCCC1 NA yes 6 0 10 5a 2004 Fukuyama OCC1=CCC[C@H](Br)[C@H]1O OCC1=CCC[C@H](Br)[C@H]1O 10 0 OCC1=CCC[C@H]2O[C@@H]12 10.Fukuyama 5a.Fukuyama C1CCCCC1 C1CCC2OC2C1 FukuyamaC1CCCCC1 FukuyamaC1CCCCC1 NA yes 7 0 5a 5 2004 Fukuyama OCC1=CCC[C@H]2O[C@@H]12 OCC1=CCC[C@H]2O[C@@H]12 9 0 CC(C)(C)[Si](C)(C)OCC1=CCC[C@H]2O[C@@H]12 5a.Fukuyama 5.Fukuyama C1CCC2OC2C1 C1CCC2OC2C1 FukuyamaC1CCCCC1 FukuyamaC1CCCCC1 ND yes 6 0 10 5 16.4 61 2004 Fukuyama OCC1=CCC[C@H](Br)[C@H]1O OCC1=CCC[C@H](Br)[C@H]1O 10 0 CC(C)(C)[Si](C)(C)OCC1=CCC[C@H]2O[C@@H]12 10.Fukuyama 5.Fukuyama C1CCCCC1 C1CCC2OC2C1 FukuyamaC1CCCCC1 FukuyamaC1CCC2OC2C1 yes 9 0 4 11 2.34 86 2004 Fukuyama COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCO[Si](C)(C)C(C)(C)C COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCO[Si](C)(C)C(C)(C)C 28 0 COC(=O)C([C@H]1CC[C@@H](O)C=C1CO[Si](C)(C)C(C)(C)C)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C 4.Fukuyama 11.Fukuyama C1CCC2NCCC2C1 C(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC1CCC2NCCC2C1 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 63-64 7 0 5 11 7.03 25.5 2004 Fukuyama CC(C)(C)[Si](C)(C)OCC1=CCC[C@H]2O[C@@H]12 CC(C)(C)[Si](C)(C)OCC1=CCC[C@H]2O[C@@H]12 16 0 COC(=O)C([C@H]1CC[C@@H](O)C=C1CO[Si](C)(C)C(C)(C)C)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C 5.Fukuyama 11.Fukuyama C1CCC2OC2C1 C(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC1CCCCC1 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 NA yes 16 0 11 12 1.93 72 2004 Fukuyama COC(=O)C([C@H]1CC[C@@H](O)C=C1CO[Si](C)(C)C(C)(C)C)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C COC(=O)C([C@H]1CC[C@@H](O)C=C1CO[Si](C)(C)C(C)(C)C)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C 44 0 COCO[C@@H]1CC[C@H](C(C(=O)OC)c2c(CCO)c3ccccc3n2C(=O)OC(C)(C)C)C(=C1)CO 11.Fukuyama 12.Fukuyama C(C1CCCCC1)C2CC3CCCCC3N2 C(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 NA yes 16 0 11 12a 2004 Fukuyama COC(=O)C([C@H]1CC[C@@H](O)C=C1CO[Si](C)(C)C(C)(C)C)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C COC(=O)C([C@H]1CC[C@@H](O)C=C1CO[Si](C)(C)C(C)(C)C)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C 44 0 COCO[C@@H]1CC[C@@H](C(=C1)CO[Si](C)(C)C(C)(C)C)C(C(=O)OC)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C 11.Fukuyama 12a.Fukuyama C(C1CCCCC1)C2CC3CCCCC3N2 C(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 yes 16 0 12a 12b 2004 Fukuyama COCO[C@@H]1CC[C@@H](C(=C1)CO[Si](C)(C)C(C)(C)C)C(C(=O)OC)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C COCO[C@@H]1CC[C@@H](C(=C1)CO[Si](C)(C)C(C)(C)C)C(C(=O)OC)(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C 47 0 COCO[C@@H]1CC[C@H](C(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C)C(=C1)CO[Si](C)(C)C(C)(C)C 12a.Fukuyama 12b.Fukuyama C(C1CCCCC1)C2CC3CCCCC3N2 C(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 ND yes 16 0 12b 12c 2004 Fukuyama COCO[C@@H]1CC[C@H](C(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C)C(=C1)CO[Si](C)(C)C(C)(C)C COCO[C@@H]1CC[C@H](C(C(=O)OC)c2[nH]c3ccccc3c2CCO[Si](C)(C)C(C)(C)C)C(=C1)CO[Si](C)(C)C(C)(C)C 43 0 COCO[C@@H]1CC[C@H](C(C(=O)OC)c2c(CCO[Si](C)(C)C(C)(C)C)c3ccccc3n2C(=O)OC(C)(C)C)C(=C1)CO[Si](C)(C)C(C)(C)C 12b.Fukuyama 12c.Fukuyama C(C1CCCCC1)C2CC3CCCCC3N2 C(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 ND yes 16 0 12c 12 2004 Fukuyama COCO[C@@H]1CC[C@H](C(C(=O)OC)c2c(CCO[Si](C)(C)C(C)(C)C)c3ccccc3n2C(=O)OC(C)(C)C)C(=C1)CO[Si](C)(C)C(C)(C)C COCO[C@@H]1CC[C@H](C(C(=O)OC)c2c(CCO[Si](C)(C)C(C)(C)C)c3ccccc3n2C(=O)OC(C)(C)C)C(=C1)CO[Si](C)(C)C(C)(C)C 50 0 COCO[C@@H]1CC[C@H](C(C(=O)OC)c2c(CCO)c3ccccc3n2C(=O)OC(C)(C)C)C(=C1)CO 12c.Fukuyama 12.Fukuyama C(C1CCCCC1)C2CC3CCCCC3N2 C(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 ND yes 16 0 12 13 1.32 95 2004 Fukuyama COCO[C@@H]1CC[C@H](C(C(=O)OC)c2c(CCO)c3ccccc3n2C(=O)OC(C)(C)C)C(=C1)CO COCO[C@@H]1CC[C@H](C(C(=O)OC)c2c(CCO)c3ccccc3n2C(=O)OC(C)(C)C)C(=C1)CO 36 0 COCO[C@@H]1CC[C@@H]2C(C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C 12.Fukuyama 13.Fukuyama C(C1CCCCC1)C2CC3CCCCC3N2 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC(C1CCCCC1)C2CC3CCCCC3N2 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 yes 20 0 13 14 1.1 69 2004 Fukuyama COCO[C@@H]1CC[C@@H]2C(C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C COCO[C@@H]1CC[C@@H]2C(C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C 47 0 COC(=O)[C@@H]1[C@H]2CCC(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 13.Fukuyama 14.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 ND yes 20 0 13 13.1 2004 Fukuyama COCO[C@@H]1CC[C@@H]2C(C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C COCO[C@@H]1CC[C@@H]2C(C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C 47 0 COCO[C@@H]1CC[C@@H]2[C@@H](C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C 13.Fukuyama 13.1.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 yes 20 0 13.1 13.2 2004 Fukuyama COCO[C@@H]1CC[C@@H]2[C@@H](C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C COCO[C@@H]1CC[C@@H]2[C@@H](C(=O)OC)c3c(CCN(CC2=C1)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-])c5ccccc5n3C(=O)OC(C)(C)C 47 0 COC(=O)[C@@H]1[C@H]2CC[C@@H](O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 13.1.Fukuyama 13.2.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 ND yes 20 0 13.2 14 2004 Fukuyama COC(=O)[C@@H]1[C@H]2CC[C@@H](O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] COC(=O)[C@@H]1[C@H]2CC[C@@H](O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 44 0 COC(=O)[C@@H]1[C@H]2CCC(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 13.2.Fukuyama 14.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 ND yes 20 0 14 15 0.641 66 2004 Fukuyama COC(=O)[C@@H]1[C@H]2CCC(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] COC(=O)[C@@H]1[C@H]2CCC(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 44 0 COC(=O)[C@@H]1[C@H]2CC(O)C(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 14.Fukuyama 15.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 148 yes 20 0 14 14.1 2004 Fukuyama COC(=O)[C@@H]1[C@H]2CCC(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] COC(=O)[C@@H]1[C@H]2CCC(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 44 0 COC(=O)[C@@H]1[C@H]2CC=C(O[Si](C)(C)C)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 14.Fukuyama 14.1.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 yes 20 0 14.1 15 2004 Fukuyama COC(=O)[C@@H]1[C@H]2CC=C(O[Si](C)(C)C)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] COC(=O)[C@@H]1[C@H]2CC=C(O[Si](C)(C)C)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 48 0 COC(=O)[C@@H]1[C@H]2CC(O)C(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 14.1.Fukuyama 15.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 ND yes 20 0 15 17 0.389 84 2004 Fukuyama COC(=O)[C@@H]1[C@H]2CC(O)C(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] COC(=O)[C@@H]1[C@H]2CC(O)C(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 45 0 COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3Nc5ccccc45)C(=O)OC 15.Fukuyama 17.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ND yes 20 0 15 16 2004 Fukuyama COC(=O)[C@@H]1[C@H]2CC(O)C(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] COC(=O)[C@@H]1[C@H]2CC(O)C(=O)C=C2CN(CCc3c1n(C(=O)OC(C)(C)C)c4ccccc34)S(=O)(=O)c5ccc(cc5)[N+](=O)[O-] 45 0 COC(=O)\C=C/1\CN(CCc2c([C@@H]([C@H]1CC=O)C(=O)OC)n(C(=O)OC(C)(C)C)c3ccccc23)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-] 15.Fukuyama 16.Fukuyama C1CCC2CC3NC4CCCCC4C3CCNCC2C1 C1CCC2NC3CCCCC3C2CCNC1 FukuyamaC1CCC2CC3NC4CCCCC4C3CCNCC2C1 FukuyamaC1CCC2NC3CCCCC3C2CCNC1 yes 16 0 16 17 2004 Fukuyama COC(=O)\C=C/1\CN(CCc2c([C@@H]([C@H]1CC=O)C(=O)OC)n(C(=O)OC(C)(C)C)c3ccccc23)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-] COC(=O)\C=C/1\CN(CCc2c([C@@H]([C@H]1CC=O)C(=O)OC)n(C(=O)OC(C)(C)C)c3ccccc23)S(=O)(=O)c4ccc(cc4)[N+](=O)[O-] 47 0 COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3Nc5ccccc45)C(=O)OC 16.Fukuyama 17.Fukuyama C1CCC2NC3CCCCC3C2CCNC1 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2NC3CCCCC3C2CCNC1 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ND yes 18 13 17 23 0.013 93 2004 Fukuyama COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3Nc5ccccc45)C(=O)OC COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3Nc5ccccc45)C(=O)OC 27 13 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 17.Fukuyama 23.Fukuyama C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 23 Strychnine 0.0355 42 2004 Fukuyama COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 23.Fukuyama Strychnine.Fukuyama C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 18 13 23 23.1 2004 Fukuyama COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 25 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 23.Fukuyama 23.1.Fukuyama C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 23.1 23.2 2004 Fukuyama COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 25 13 O=C1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23.1.Fukuyama 23.2.Fukuyama C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 FukuyamaC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 FukuyamaC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 23.2 23.3 2004 Fukuyama O=C1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 O=C1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23.2.Fukuyama 23.3.Fukuyama C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 FukuyamaC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 FukuyamaC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 23.3 Strychnine 42 2004 Fukuyama OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 23.3.Fukuyama Strychnine.Fukuyama C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 FukuyamaC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 FukuyamaC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 24 25 Strychnine 2004 Fukuyama O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Fukuyama C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 FukuyamaC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . 265-270 yes 6 0 SilylCyclohexenol 3i 1 88 2003 Mori CC(C)(C)[Si](C)(C)OCC1=CCCCC1O CC(C)(C)[Si](C)(C)OCC1=CCCCC1O 16 0 CCOP(=O)(OCC)OC1CCCC=C1CO[Si](C)(C)C(C)(C)C SilylCyclohexenol.Mori 3i.Mori C1CCCCC1 C1CCCCC1 MoriC1CCCCC1 MoriC1CCCCC1 no 6 0 3i 7b 80 2003 Mori CCOP(=O)(OCC)OC1CCCC=C1CO[Si](C)(C)C(C)(C)C CCOP(=O)(OCC)OC1CCCC=C1CO[Si](C)(C)C(C)(C)C 24 0 Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CO[Si](C)(C)C(C)(C)C)c3ccccc3Br 3i.Mori 7b.Mori C1CCCCC1 C1CCC(CC1)NC2CCCCC2 MoriC1CCCCC1 MoriC1CCC(CC1)NC2CCCCC2 no 13 0 7b 7b.1 0.241 100 2003 Mori Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CO[Si](C)(C)C(C)(C)C)c3ccccc3Br Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CO[Si](C)(C)C(C)(C)C)c3ccccc3Br 33 0 Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CO)c3ccccc3Br 7b.Mori 7b.1.Mori C1CCC(CC1)NC2CCCCC2 C1CCC(CC1)NC2CCCCC2 MoriC1CCC(CC1)NC2CCCCC2 MoriC1CCC(CC1)NC2CCCCC2 yes 13 0 7b.1 7b.2 24.1 90 2003 Mori Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CO)c3ccccc3Br Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CO)c3ccccc3Br 26 0 Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CBr)c3ccccc3Br 7b.1.Mori 7b.2.Mori C1CCC(CC1)NC2CCCCC2 C1CCC(CC1)NC2CCCCC2 MoriC1CCC(CC1)NC2CCCCC2 MoriC1CCC(CC1)NC2CCCCC2 yes 13 0 7b.2 9 1.8 95 2003 Mori Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CBr)c3ccccc3Br Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CBr)c3ccccc3Br 26 0 Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CC#N)c3ccccc3Br 7b.2.Mori 9.Mori C1CCC(CC1)NC2CCCCC2 C1CCC(CC1)NC2CCCCC2 MoriC1CCC(CC1)NC2CCCCC2 MoriC1CCC(CC1)NC2CCCCC2 yes 13 0 9 10 2.25 73 2003 Mori Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CC#N)c3ccccc3Br Cc1ccc(cc1)S(=O)(=O)N([C@H]2CCCC=C2CC#N)c3ccccc3Br 27 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CC#N)c4ccccc24 9.Mori 10.Mori C1CCC(CC1)NC2CCCCC2 C1CCC2C(C1)NC3CCCCC23 MoriC1CCC(CC1)NC2CCCCC2 MoriC1CCC2C(C1)NC3CCCCC23 yes 13 0 10 11 10.4 66 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CC#N)c4ccccc24 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CC#N)c4ccccc24 26 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CCNC(=O)OC(C)(C)C)c4ccccc24 10.Mori 11.Mori C1CCC2C(C1)NC3CCCCC23 C1CCC2C(C1)NC3CCCCC23 MoriC1CCC2C(C1)NC3CCCCC23 MoriC1CCC2C(C1)NC3CCCCC23 yes 13 0 10 10.1 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CC#N)c4ccccc24 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CC#N)c4ccccc24 26 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CCN)c4ccccc24 10.Mori 10.1.Mori C1CCC2C(C1)NC3CCCCC23 C1CCC2C(C1)NC3CCCCC23 MoriC1CCC2C(C1)NC3CCCCC23 MoriC1CCC2C(C1)NC3CCCCC23 yes 13 0 10.1 11 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CCN)c4ccccc24 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CCN)c4ccccc24 26 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CCNC(=O)OC(C)(C)C)c4ccccc24 10.1.Mori 11.Mori C1CCC2C(C1)NC3CCCCC23 C1CCC2C(C1)NC3CCCCC23 MoriC1CCC2C(C1)NC3CCCCC23 MoriC1CCC2C(C1)NC3CCCCC23 yes 13 0 11 14 7.26 77 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CCNC(=O)OC(C)(C)C)c4ccccc24 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CCC=C[C@@]3(CCNC(=O)OC(C)(C)C)c4ccccc24 33 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC=C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 11.Mori 14.Mori C1CCC2C(C1)NC3CCCCC23 C1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCCC23 MoriC1CCC2C(C1)NC3CCCC4NCCC234 yes 16 0 14 16 5.31 80 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC=C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC=C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 33 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC(O)C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 14.Mori 16.Mori C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 yes 16 0 16 13 4.25 87 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC(O)C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC(O)C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 34 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC(=O)C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 16.Mori 13.Mori C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 yes 16 0 13 17 0.377 63 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC(=O)C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C Cc1ccc(cc1)S(=O)(=O)N2[C@H]3CC(=O)C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 34 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3C=C(C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)OS(=O)(=O)C(F)(F)F 13.Mori 17.Mori C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 ND yes 16 0 17 19 0.241 100 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3C=C(C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)OS(=O)(=O)C(F)(F)F Cc1ccc(cc1)S(=O)(=O)N2[C@H]3C=C(C[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C)OS(=O)(=O)C(F)(F)F 41 0 Cc1ccc(cc1)S(=O)(=O)N2[C@H]3C=CC[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 17.Mori 19.Mori C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 yes 16 0 19 19.1 0.069 89 2003 Mori Cc1ccc(cc1)S(=O)(=O)N2[C@H]3C=CC[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C Cc1ccc(cc1)S(=O)(=O)N2[C@H]3C=CC[C@@H]4N(CC[C@]34c5ccccc25)C(=O)OC(C)(C)C 33 0 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H](Nc4ccccc24)C=CC[C@H]13 19.Mori 19.1.Mori C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 yes 16 0 19.1 25 0.0614 66 2003 Mori CC(C)(C)OC(=O)N1CC[C@@]23[C@@H](Nc4ccccc24)C=CC[C@H]13 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H](Nc4ccccc24)C=CC[C@H]13 23 0 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C[C@@H]2N(C(=O)\C=C/Br)c4ccccc34 19.1.Mori 25.Mori C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)NC3CCCC4NCCC234 yes 16 0 25 26 0.0337 46 2003 Mori CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C[C@@H]2N(C(=O)\C=C/Br)c4ccccc34 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C[C@@H]2N(C(=O)\C=C/Br)c4ccccc34 28 0 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1C=CC4C=CC(=O)N([C@H]24)c5ccccc35 25.Mori 26.Mori C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)NC3CCCC4NCCC234 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 yes 19 0 26.1 27 0.187 66 2003 Mori CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 27 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 26.1.Mori 27.Mori C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 yes 19 0 26 26.1 0.023 81 2003 Mori CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1C=CC4C=CC(=O)N([C@H]24)c5ccccc35 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1C=CC4C=CC(=O)N([C@H]24)c5ccccc35 27 0 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 26.Mori 26.1.Mori C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 yes 19 0 26.1 26.2 2003 Mori CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 CC(C)(C)OC(=O)N1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 27 0 O=C1C=CC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 26.1.Mori 26.2.Mori C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 yes 19 0 26.2 27 2003 Mori O=C1C=CC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 O=C1C=CC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 20 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 26.2.Mori 27.Mori C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 yes 19 0 27 28 0.0153 48 2003 Mori CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 33 0 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=C3N(C(=O)C=C5)c6ccccc46 27.Mori 28.Mori C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 MoriC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 MoriC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 yes 21 13 28 28.1 0.0132 47 2003 Mori CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=C3N(C(=O)C=C5)c6ccccc46 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=C3N(C(=O)C=C5)c6ccccc46 32 13 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 28.Mori 28.1.Mori C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 MoriC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 MoriC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 yes 21 13 28.1 (+)isostrychnine 0.0437 96 2003 Mori CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 32 13 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 28.1.Mori (+)isostrychnine.Mori C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 MoriC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 MoriC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 yes 21 13 (+)isostrychnine Strychnine 0.0586 16 2003 Mori OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 (+)isostrychnine.Mori Strychnine.Mori C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 MoriC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 MoriC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 24 25 Strychnine 2003 Mori O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Mori C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 MoriC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . yes 9 0 5 6 53.6 100 2002 Bodwell NCCc1c[nH]c2ccccc12 NCCc1c[nH]c2ccccc12 12 0 Ic1ccc(NCCc2c[nH]c3ccccc23)nn1 5.Bodwell 6.Bodwell C1CCC2NCCC2C1 C(CC1CNC2CCCCC12)NC3CCCNN3 BodwellC1CCC2NCCC2C1 BodwellC(CC1CNC2CCCCC12)NC3CCCNN3 18 0 6 7 10 91 2002 Bodwell Ic1ccc(NCCc2c[nH]c3ccccc23)nn1 Ic1ccc(NCCc2c[nH]c3ccccc23)nn1 19 0 Ic1ccc(NCCc2cn(CC=C)c3ccccc23)nn1 6.Bodwell 7.Bodwell C(CC1CNC2CCCCC12)NC3CCCNN3 C(CC1CNC2CCCCC12)NC3CCCNN3 BodwellC(CC1CNC2CCCCC12)NC3CCCNN3 BodwellC(CC1CNC2CCCCC12)NC3CCCNN3 173-5 18 0 7 8 5 65 2002 Bodwell Ic1ccc(NCCc2cn(CC=C)c3ccccc23)nn1 Ic1ccc(NCCc2cn(CC=C)c3ccccc23)nn1 22 0 C1Cc2ccc(NCCc3cn(C1)c4ccccc34)nn2 7.Bodwell 8.Bodwell C(CC1CNC2CCCCC12)NC3CCCNN3 C1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 BodwellC(CC1CNC2CCCCC12)NC3CCCNN3 BodwellC1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 171-2 21 19 8 9 1 96 2002 Bodwell C1Cc2ccc(NCCc3cn(C1)c4ccccc34)nn2 C1Cc2ccc(NCCc3cn(C1)c4ccccc34)nn2 21 19 COC(=O)N1CCc2cn(CCCc3ccc1nn3)c4ccccc24 8.Bodwell 9.Bodwell C1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 C1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 BodwellC1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 BodwellC1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 21 19 9 10 0.892 100 2002 Bodwell COC(=O)N1CCc2cn(CCCc3ccc1nn3)c4ccccc24 COC(=O)N1CCc2cn(CCCc3ccc1nn3)c4ccccc24 25 19 COC(=O)N1CC[C@]23C4N(CCCC4=CC=C12)c5ccccc35 9.Bodwell 10.Bodwell C1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)C3CCNC4CCC(CCCN2C3)NN4 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 19 0 10 11 0.29 100 2002 Bodwell COC(=O)N1CC[C@]23C4N(CCCC4=CC=C12)c5ccccc35 COC(=O)N1CC[C@]23C4N(CCCC4=CC=C12)c5ccccc35 23 0 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCCN(C24)c5ccccc35 10.Bodwell 11.Bodwell C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 182-3 no 19 0 11 12 0.26 30 2002 Bodwell COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCCN(C24)c5ccccc35 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCCN(C24)c5ccccc35 23 0 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N(C24)c5ccccc35 11.Bodwell 12.Bodwell C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 12 13 0.029 93 2002 Bodwell COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N(C24)c5ccccc35 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N(C24)c5ccccc35 24 0 O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 12.Bodwell 13.Bodwell C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 182-4 no 19 0 13 2002 Bodwell O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 O=C1CCC2=CC[C@@H]3NCC[C@]34C2N1c5ccccc45 20 0 13.Bodwell C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 BodwellC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 . no 6 0 6 5 6000 91 2002 Shibasaki O=C1CCCC=C1 O=C1CCCC=C1 7 0 COC(=O)C([C@@H]1CCCC(=O)C1)C(=O)OC 6.Shibasaki 5.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 6 0 5 8 1000 97 2002 Shibasaki COC(=O)C([C@@H]1CCCC(=O)C1)C(=O)OC COC(=O)C([C@@H]1CCCC(=O)C1)C(=O)OC 16 0 COC(=O)C[C@@H]1CCCC2(C1)OCCO2 5.Shibasaki 8.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 54.5-55.5 yes 6 0 5 5.1 2002 Shibasaki COC(=O)C([C@@H]1CCCC(=O)C1)C(=O)OC COC(=O)C([C@@H]1CCCC(=O)C1)C(=O)OC 16 0 COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)OC 5.Shibasaki 5.1.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 5.1 8 2002 Shibasaki COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)OC COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)OC 19 0 COC(=O)C[C@@H]1CCCC2(C1)OCCO2 5.1.Shibasaki 8.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 8 9 84.8 72 2002 Shibasaki COC(=O)C[C@@H]1CCCC2(C1)OCCO2 COC(=O)C[C@@H]1CCCC2(C1)OCCO2 15 0 COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)COCc3ccc(OC)cc3 8.Shibasaki 9.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 9 10 44.5 70 2002 Shibasaki COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)COCc3ccc(OC)cc3 COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)COCc3ccc(OC)cc3 28 0 COC(=O)\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CCCC3(C2)OCCO3 9.Shibasaki 10.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 9 9.1 2002 Shibasaki COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)COCc3ccc(OC)cc3 COC(=O)C([C@@H]1CCCC2(C1)OCCO2)C(=O)COCc3ccc(OC)cc3 28 0 COC(=O)C(C(O)COCc1ccc(OC)cc1)[C@@H]2CCCC3(C2)OCCO3 9.Shibasaki 9.1.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 9.1 10 2002 Shibasaki COC(=O)C(C(O)COCc1ccc(OC)cc1)[C@@H]2CCCC3(C2)OCCO3 COC(=O)C(C(O)COCc1ccc(OC)cc1)[C@@H]2CCCC3(C2)OCCO3 28 0 COC(=O)\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CCCC3(C2)OCCO3 9.1.Shibasaki 10.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 10 TIPS-ether 7.98 98 2002 Shibasaki COC(=O)\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CCCC3(C2)OCCO3 COC(=O)\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CCCC3(C2)OCCO3 27 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC3(C2)OCCO3)cc1 10.Shibasaki TIPS-ether.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 10 10.1 2002 Shibasaki COC(=O)\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CCCC3(C2)OCCO3 COC(=O)\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CCCC3(C2)OCCO3 27 0 COc1ccc(COC\C=C(\CO)/[C@@H]2CCCC3(C2)OCCO3)cc1 10.Shibasaki 10.1.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 10.1 TIPS-ether 2002 Shibasaki COc1ccc(COC\C=C(\CO)/[C@@H]2CCCC3(C2)OCCO3)cc1 COc1ccc(COC\C=C(\CO)/[C@@H]2CCCC3(C2)OCCO3)cc1 25 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC3(C2)OCCO3)cc1 10.1.Shibasaki TIPS-ether.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 TIPS-ether 11 14.3 62 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC3(C2)OCCO3)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC3(C2)OCCO3)cc1 35 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC(=O)C2)cc1 TIPS-ether.Shibasaki 11.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 TIPS-ether TIPS-ether 31 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC3(C2)OCCO3)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC3(C2)OCCO3)cc1 35 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC3(C2)OCCO3)cc1 TIPS-ether.Shibasaki TIPS-ether.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 11 12 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC(=O)C2)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC(=O)C2)cc1 32 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCC=C(C2)O[Si](C)(C)C)cc1 11.Shibasaki 12.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 12 13 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCC=C(C2)O[Si](C)(C)C)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCC=C(C2)O[Si](C)(C)C)cc1 36 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)C2)cc1 12.Shibasaki 13.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 11 13 0.873 90 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC(=O)C2)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CCCC(=O)C2)cc1 32 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)C2)cc1 11.Shibasaki 13.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 13 14a 3.47 57 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)C2)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)C2)cc1 32 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)[C@H]2CO)cc1 13.Shibasaki 14a.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 13 13.1 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)C2)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)C2)cc1 32 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=C2)O[Si](C)(C)C)cc1 13.Shibasaki 13.1.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 13.1 14a 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=C2)O[Si](C)(C)C)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=C2)O[Si](C)(C)C)cc1 36 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)[C@H]2CO)cc1 13.1.Shibasaki 14a.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 14a 15 8.9 89 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)[C@H]2CO)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=CC(=O)[C@H]2CO)cc1 34 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(I)C(=O)[C@H]2CO)cc1 14a.Shibasaki 15.Shibasaki C1CCCCC1 C1CCCCC1 ShibasakiC1CCCCC1 ShibasakiC1CCCCC1 yes 6 0 15 16 0.244 100 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(I)C(=O)[C@H]2CO)cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(I)C(=O)[C@H]2CO)cc1 35 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(C(=O)[C@H]2CO)c3ccccc3[N+](=O)[O-])cc1 15.Shibasaki 16.Shibasaki C1CCCCC1 C1CCC(CC1)C2CCCCC2 ShibasakiC1CCCCC1 ShibasakiC1CCC(CC1)C2CCCCC2 yes 12 0 16 16-SEM 0.205 100 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(C(=O)[C@H]2CO)c3ccccc3[N+](=O)[O-])cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(C(=O)[C@H]2CO)c3ccccc3[N+](=O)[O-])cc1 43 0 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 16.Shibasaki 16-SEM.Shibasaki C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C2CCCCC2 ShibasakiC1CCC(CC1)C2CCCCC2 ShibasakiC1CCC(CC1)C2CCCCC2 yes 12 0 16-SEM 4 0.346 100 2002 Shibasaki COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 COc1ccc(COC\C=C(\CO[Si](C(C)C)(C(C)C)C(C)C)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 49 0 COc1ccc(COC\C=C(\CO)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 16-SEM.Shibasaki 4.Shibasaki C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C2CCCCC2 ShibasakiC1CCC(CC1)C2CCCCC2 ShibasakiC1CCC(CC1)C2CCCCC2 yes 12 0 4 3 0.133 77 2002 Shibasaki COc1ccc(COC\C=C(\CO)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 COc1ccc(COC\C=C(\CO)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 39 0 CCSC(CN1C\C(=C\COCc2ccc(OC)cc2)\[C@@H]3C[C@H]1c4c([nH]c5ccccc45)[C@H]3COCC[Si](C)(C)C)SCC 4.Shibasaki 3.Shibasaki C1CCC(CC1)C2CCCCC2 C1CCC2C(C1)NC3CC4CCNC(C4)C23 ShibasakiC1CCC(CC1)C2CCCCC2 ShibasakiC1CCC2C(C1)NC3CC4CCNC(C4)C23 64-65 yes 12 0 4 4.1 2002 Shibasaki COc1ccc(COC\C=C(\CO)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 COc1ccc(COC\C=C(\CO)/[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])cc1 39 0 CCSC(CNC\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])SCC 4.Shibasaki 4.1.Shibasaki C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C2CCCCC2 ShibasakiC1CCC(CC1)C2CCCCC2 ShibasakiC1CCC(CC1)C2CCCCC2 yes 12 0 4.1 3 2002 Shibasaki CCSC(CNC\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])SCC CCSC(CNC\C(=C\COCc1ccc(OC)cc1)\[C@@H]2CC=C(C(=O)[C@H]2COCC[Si](C)(C)C)c3ccccc3[N+](=O)[O-])SCC 47 0 CCSC(CN1C\C(=C\COCc2ccc(OC)cc2)\[C@@H]3C[C@H]1c4c([nH]c5ccccc45)[C@H]3COCC[Si](C)(C)C)SCC 4.1.Shibasaki 3.Shibasaki C1CCC(CC1)C2CCCCC2 C1CCC2C(C1)NC3CC4CCNC(C4)C23 ShibasakiC1CCC(CC1)C2CCCCC2 ShibasakiC1CCC2C(C1)NC3CC4CCNC(C4)C23 yes 16 10 3 18 0.161 86 2002 Shibasaki CCSC(CN1C\C(=C\COCc2ccc(OC)cc2)\[C@@H]3C[C@H]1c4c([nH]c5ccccc45)[C@H]3COCC[Si](C)(C)C)SCC CCSC(CN1C\C(=C\COCc2ccc(OC)cc2)\[C@@H]3C[C@H]1c4c([nH]c5ccccc45)[C@H]3COCC[Si](C)(C)C)SCC 44 10 CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15C(=Nc6ccccc56)[C@H]4COCC[Si](C)(C)C 3.Shibasaki 18.Shibasaki C1CCC2C(C1)NC3CC4CCNC(C4)C23 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCNC(C4)C23 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 18 2 0.0375 68 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15C(=Nc6ccccc56)[C@H]4COCC[Si](C)(C)C CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15C(=Nc6ccccc56)[C@H]4COCC[Si](C)(C)C 41 13 CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15[C@@H](Nc6ccccc56)[C@H]4COCC[Si](C)(C)C 18.Shibasaki 2.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 2 19 0.0433 51 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15[C@@H](Nc6ccccc56)[C@H]4COCC[Si](C)(C)C CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15[C@@H](Nc6ccccc56)[C@H]4COCC[Si](C)(C)C 41 13 CCS[C@@H]1CN2C\C(=C\CO[Si](C(C)C)(C(C)C)C(C)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 2.Shibasaki 19.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 2 2.1 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15[C@@H](Nc6ccccc56)[C@H]4COCC[Si](C)(C)C CCS[C@@H]1CN2C\C(=C\COCc3ccc(OC)cc3)\[C@@H]4C[C@H]2[C@@]15[C@@H](Nc6ccccc56)[C@H]4COCC[Si](C)(C)C 41 13 CCS[C@@H]1CN2C\C(=C\CO)\[C@@H]3C[C@H]2[C@@]14[C@@H](Nc5ccccc45)[C@H]3CO 2.Shibasaki 2.1.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 2.1 2.2 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\CO)\[C@@H]3C[C@H]2[C@@]14[C@@H](Nc5ccccc45)[C@H]3CO CCS[C@@H]1CN2C\C(=C\CO)\[C@@H]3C[C@H]2[C@@]14[C@@H](Nc5ccccc45)[C@H]3CO 26 13 CCS[C@@H]1CN2C\C(=C\COC(=O)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3COC(=O)C)N(C(=O)C)c5ccccc45 2.1.Shibasaki 2.2.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 2.2 2.3 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\COC(=O)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3COC(=O)C)N(C(=O)C)c5ccccc45 CCS[C@@H]1CN2C\C(=C\COC(=O)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3COC(=O)C)N(C(=O)C)c5ccccc45 35 13 CCS[C@@H]1CN2C\C(=C\CO)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 2.2.Shibasaki 2.3.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 2.3 19 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\CO)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 CCS[C@@H]1CN2C\C(=C\CO)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 29 13 CCS[C@@H]1CN2C\C(=C\CO[Si](C(C)C)(C(C)C)C(C)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 2.3.Shibasaki 19.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ND yes 18 13 19 20 0.018 33 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\CO[Si](C(C)C)(C(C)C)C(C)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 CCS[C@@H]1CN2C\C(=C\CO[Si](C(C)C)(C(C)C)C(C)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 39 13 CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](CO)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C 19.Shibasaki 20.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 90-94 yes 18 13 19 19 65 2002 Shibasaki CCS[C@@H]1CN2C\C(=C\CO[Si](C(C)C)(C(C)C)C(C)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 CCS[C@@H]1CN2C\C(=C\CO[Si](C(C)C)(C(C)C)C(C)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 39 13 CCS[C@@H]1CN2C\C(=C\CO[Si](C(C)C)(C(C)C)C(C)C)\[C@@H]3C[C@H]2[C@@]14[C@H]([C@H]3CO)N(C(=O)C)c5ccccc45 19.Shibasaki 19.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 20 21 0.011 83 2002 Shibasaki CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](CO)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](CO)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C 36 13 CC(=O)N1[C@H]2[C@@H]3C(O)OCC=C4CN5CC[C@]2([C@@H]5C[C@H]34)c6ccccc16 20.Shibasaki 21.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 18 13 20 20.1 2002 Shibasaki CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](CO)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](CO)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C 36 13 CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](C=O)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C 20.Shibasaki 20.1.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 20.1 21 2002 Shibasaki CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](C=O)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C CC(C)[Si](OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H](C=O)[C@@H]3N(C(=O)C)c5ccccc45)(C(C)C)C(C)C 36 13 CC(=O)N1[C@H]2[C@@H]3C(O)OCC=C4CN5CC[C@]2([C@@H]5C[C@H]34)c6ccccc16 20.1.Shibasaki 21.Shibasaki C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ShibasakiC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 ShibasakiC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 21 Strychnine 0.0369 42 2002 Shibasaki CC(=O)N1[C@H]2[C@@H]3C(O)OCC=C4CN5CC[C@]2([C@@H]5C[C@H]34)c6ccccc16 CC(=O)N1[C@H]2[C@@H]3C(O)OCC=C4CN5CC[C@]2([C@@H]5C[C@H]34)c6ccccc16 26 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 21.Shibasaki Strychnine.Shibasaki C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 ShibasakiC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ShibasakiC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 182-5 yes 22 18 21 Wieland Gumlich Aldehyde 2002 Shibasaki CC(=O)N1[C@H]2[C@@H]3C(O)OCC=C4CN5CC[C@]2([C@@H]5C[C@H]34)c6ccccc16 CC(=O)N1[C@H]2[C@@H]3C(O)OCC=C4CN5CC[C@]2([C@@H]5C[C@H]34)c6ccccc16 26 18 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 21.Shibasaki Wieland Gumlich Aldehyde.Shibasaki C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ShibasakiC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ShibasakiC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 Wieland Gumlich Aldehyde Strychnine 2002 Shibasaki OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 Wieland Gumlich Aldehyde.Shibasaki Strychnine.Shibasaki C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 ShibasakiC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 ShibasakiC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 24 25 Strychnine 2002 Shibasaki O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Shibasaki C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 ShibasakiC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . yes 6 0 Butenoic acid Butenoic acid chloride 17.4 2001 Martin OC(=O)\C=C\COCc1ccccc1 OC(=O)\C=C\COCc1ccccc1 14 0 ClC(=O)\C=C\COCc1ccccc1 Butenoic acid.Martin Butenoic acid chloride.Martin C1CCCCC1 C1CCCCC1 MartinC1CCCCC1 MartinC1CCCCC1 6 0 Butenoic acid chloride 30 2001 Martin ClC(=O)\C=C\COCc1ccccc1 ClC(=O)\C=C\COCc1ccccc1 14 0 O=C\C=C\CC1N(CCc2c1[nH]c3ccccc23)C(=O)\C=C\COCc4ccccc4 Butenoic acid chloride.Martin 30.Martin C1CCCCC1 C1CCC2C(C1)NC3CNCCC23 MartinC1CCCCC1 MartinC1CCC2C(C1)NC3CNCCC23 na 13 0 6 30 15.7 79 2001 Martin C1Cc2c(C=N1)[nH]c3ccccc23 C1Cc2c(C=N1)[nH]c3ccccc23 13 0 O=C\C=C\CC1N(CCc2c1[nH]c3ccccc23)C(=O)\C=C\COCc4ccccc4 6.Martin 30.Martin C1CCC2C(C1)NC3CNCCC23 C1CCC2C(C1)NC3CNCCC23 MartinC1CCC2C(C1)NC3CNCCC23 MartinC1CCC2C(C1)NC3CNCCC23 13 0 30 31 3 85 2001 Martin O=C\C=C\CC1N(CCc2c1[nH]c3ccccc23)C(=O)\C=C\COCc4ccccc4 O=C\C=C\CC1N(CCc2c1[nH]c3ccccc23)C(=O)\C=C\COCc4ccccc4 31 0 O=C1[C@H]2[C@H](COCc3ccccc3)OC=C[C@H]2C[C@@H]4N1CCc5c4[nH]c6ccccc56 30.Martin 31.Martin C1CCC2C(C1)NC3CNCCC23 C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3CNCCC23 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 118-9 no 21 0 31 31.1 2.2 93 2001 Martin O=C1[C@H]2[C@H](COCc3ccccc3)OC=C[C@H]2C[C@@H]4N1CCc5c4[nH]c6ccccc56 O=C1[C@H]2[C@H](COCc3ccccc3)OC=C[C@H]2C[C@@H]4N1CCc5c4[nH]c6ccccc56 31 0 OC1C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@H]2[C@H](COCc6ccccc6)O1 31.Martin 31.1.Martin C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 236-8 no 21 0 31.1 32 1.19 79 2001 Martin OC1C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@H]2[C@H](COCc6ccccc6)O1 OC1C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@H]2[C@H](COCc6ccccc6)O1 32 0 O=C1C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@H]2[C@H](COCc6ccccc6)O1 31.1.Martin 32.Martin C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 no 21 0 32 37 0.465 67 2001 Martin O=C1C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@H]2[C@H](COCc6ccccc6)O1 O=C1C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@H]2[C@H](COCc6ccccc6)O1 32 0 OC[C@@H]1OC(=O)C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@@H]12 32.Martin 37.Martin C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 210-2 no 21 0 37 alcohol 0.22 74 2001 Martin OC[C@@H]1OC(=O)C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@@H]12 OC[C@@H]1OC(=O)C[C@H]2C[C@@H]3N(CCc4c3[nH]c5ccccc45)C(=O)[C@@H]12 25 0 COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C(=O)/C/1=C/CO 37.Martin alcohol.Martin C1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 C1CCC2C(C1)NC3C2CCN4CCCCC34 MartinC1CCC2C(C1)NC3C2CCN4CC5COCCC5CC34 MartinC1CCC2C(C1)NC3C2CCN4CCCCC34 264-5 no 17 0 alcohol 39 0.17 71 2001 Martin COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C(=O)/C/1=C/CO COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C(=O)/C/1=C/CO 26 0 COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C(=O)/C/1=C/CO[Si](C)(C)C(C)(C)C alcohol.Martin 39.Martin C1CCC2C(C1)NC3C2CCN4CCCCC34 C1CCC2C(C1)NC3C2CCN4CCCCC34 MartinC1CCC2C(C1)NC3C2CCN4CCCCC34 MartinC1CCC2C(C1)NC3C2CCN4CCCCC34 337-9 no 17 0 39 40 1.2 83 2001 Martin COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C(=O)/C/1=C/CO[Si](C)(C)C(C)(C)C COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C(=O)/C/1=C/CO[Si](C)(C)C(C)(C)C 33 0 COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C/C/1=C/CO[Si](C)(C)C(C)(C)C 39.Martin 40.Martin C1CCC2C(C1)NC3C2CCN4CCCCC34 C1CCC2C(C1)NC3C2CCN4CCCCC34 MartinC1CCC2C(C1)NC3C2CCN4CCCCC34 MartinC1CCC2C(C1)NC3C2CCN4CCCCC34 200-201 no 17 0 40 silyl ether 0.15 26 2001 Martin COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C/C/1=C/CO[Si](C)(C)C(C)(C)C COC(=O)CC1C[C@@H]2N(CCc3c2[nH]c4ccccc34)C/C/1=C/CO[Si](C)(C)C(C)(C)C 32 0 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 40.Martin silyl ether.Martin C1CCC2C(C1)NC3C2CCN4CCCCC34 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MartinC1CCC2C(C1)NC3C2CCN4CCCCC34 MartinC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 43 no 18 13 silyl ether 36 0.038 83 2001 Martin COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]45 32 13 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 silyl ether.Martin 36.Martin C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MartinC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MartinC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 147-9 no 18 13 36 2001 Martin COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 25 13 36.Martin C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MartinC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 . no 9 0 N-AcetylTryptamine 3 4.46 86 2000 Vollhardt CC(=O)NCCc1c[nH]c2ccccc12 CC(=O)NCCc1c[nH]c2ccccc12 15 0 CC(=O)NCCc1cn(C(=O)\C=C/C#C)c2ccccc12 N-AcetylTryptamine.Vollhardt 3.Vollhardt C1CCC2NCCC2C1 C1CCC2NCCC2C1 VollhardtC1CCC2NCCC2C1 VollhardtC1CCC2NCCC2C1 9 0 3 4 3.57 46 2000 Vollhardt CC(=O)NCCc1cn(C(=O)\C=C/C#C)c2ccccc12 CC(=O)NCCc1cn(C(=O)\C=C/C#C)c2ccccc12 21 0 CC(=O)NCC[C@@]12C3C4C5C6(C=CC(=O)N([C@H]16)c7ccccc27)[Co]345C8C=CC=C8 3.Vollhardt 4.Vollhardt C1CCC2NCCC2C1 C1CCC2C(C1)C3CCCC4CCCN2C34 VollhardtC1CCC2NCCC2C1 VollhardtC1CCC2C(C1)C3CCCC4CCCN2C34 110 16 0 4 7 6.1 93 2000 Vollhardt CC(=O)NCC[C@@]12C3C4C5C6(C=CC(=O)N([C@H]16)c7ccccc27)[Co]345C8C=CC=C8 CC(=O)NCC[C@@]12C3C4C5C6(C=CC(=O)N([C@H]16)c7ccccc27)[Co]345C8C=CC=C8 29 0 NCC[C@@]12C3C4C5C6(C=CC(=O)N([C@H]16)c7ccccc27)[Co]345C8C=CC=C8 4.Vollhardt 7.Vollhardt C1CCC2C(C1)C3CCCC4CCCN2C34 C1CCC2C(C1)C3CCCC4CCCN2C34 VollhardtC1CCC2C(C1)C3CCCC4CCCN2C34 VollhardtC1CCC2C(C1)C3CCCC4CCCN2C34 no 16 0 7 8 1.78 77 2000 Vollhardt NCC[C@@]12C3C4C5C6(C=CC(=O)N([C@H]16)c7ccccc27)[Co]345C8C=CC=C8 NCC[C@@]12C3C4C5C6(C=CC(=O)N([C@H]16)c7ccccc27)[Co]345C8C=CC=C8 26 0 O=C1CC=C2C=C[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 7.Vollhardt 8.Vollhardt C1CCC2C(C1)C3CCCC4CCCN2C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 VollhardtC1CCC2C(C1)C3CCCC4CCCN2C34 VollhardtC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 8 vinyl iodide 0.625 74 2000 Vollhardt O=C1CC=C2C=C[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 O=C1CC=C2C=C[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 20 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1C=CC4=CCC(=O)N([C@H]24)c5ccccc35 8.Vollhardt vinyl iodide.Vollhardt C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 VollhardtC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 VollhardtC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 169 no 19 0 vinyl iodide 9 0.279 90 2000 Vollhardt CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1C=CC4=CCC(=O)N([C@H]24)c5ccccc35 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1C=CC4=CCC(=O)N([C@H]24)c5ccccc35 33 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 vinyl iodide.Vollhardt 9.Vollhardt C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 VollhardtC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 VollhardtC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 80-2 no 19 0 9 10 0.07 37 2000 Vollhardt CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 33 0 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 9.Vollhardt 10.Vollhardt C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 VollhardtC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 VollhardtC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 115-7 no 21 13 10 13 0.045 99 2000 Vollhardt CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 32 13 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 10.Vollhardt 13.Vollhardt C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 VollhardtC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 VollhardtC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 13 2000 Vollhardt OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 25 13 13.Vollhardt C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 VollhardtC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 . 229-30 no 19 0 9 12 0.12 46 2000 Vollhardt CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4C=CC(=O)N([C@H]24)c5ccccc35 33 0 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=C3N(C(=O)C=C5)c6ccccc46 9.Vollhardt 12.Vollhardt C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 VollhardtC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 VollhardtC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 12 10 0.016 54 2000 Vollhardt CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=C3N(C(=O)C=C5)c6ccccc46 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=C3N(C(=O)C=C5)c6ccccc46 32 13 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 12.Vollhardt 10.Vollhardt C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 VollhardtC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 VollhardtC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 6 0 2 3 160 72 2000 Bonjoch OC1=CC(=O)CCC1 OC1=CC(=O)CCC1 8 0 OC1=C(C(=O)CCC1)c2ccccc2[N+](=O)[O-] 2.Bonjoch 3.Bonjoch C1CCCCC1 C1CCC(CC1)C2CCCCC2 BonjochC1CCCCC1 BonjochC1CCC(CC1)C2CCCCC2 229-30 12 0 3 8 89.7 85 2000 Bonjoch OC1=C(C(=O)CCC1)c2ccccc2[N+](=O)[O-] OC1=C(C(=O)CCC1)c2ccccc2[N+](=O)[O-] 17 0 [O-][N+](=O)c1ccccc1C2=C(CCCC2=O)OCC=C 3.Bonjoch 8.Bonjoch C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C2CCCCC2 208-9 12 0 8 17 16.3 80 2000 Bonjoch [O-][N+](=O)c1ccccc1C2=C(CCCC2=O)OCC=C [O-][N+](=O)c1ccccc1C2=C(CCCC2=O)OCC=C 20 0 [O-][N+](=O)c1ccccc1C2(CC=C)C(=O)CCCC2=O 8.Bonjoch 17.Bonjoch C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C2CCCCC2 12 0 17 18 18.3 37 2000 Bonjoch [O-][N+](=O)c1ccccc1C2(CC=C)C(=O)CCCC2=O [O-][N+](=O)c1ccccc1C2(CC=C)C(=O)CCCC2=O 20 0 C[C@H](N1CC[C@]2([C@@H]1CCCC2=O)c3ccccc3[N+](=O)[O-])c4ccccc4 17.Bonjoch 18.Bonjoch C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C23CCCCC2NCC3 161-3 12 0 17 17.1 2000 Bonjoch [O-][N+](=O)c1ccccc1C2(CC=C)C(=O)CCCC2=O [O-][N+](=O)c1ccccc1C2(CC=C)C(=O)CCCC2=O 20 0 [O-][N+](=O)c1ccccc1C2(CC=O)C(=O)CCCC2=O 17.Bonjoch 17.1.Bonjoch C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C2CCCCC2 12 0 17.1 18 2000 Bonjoch [O-][N+](=O)c1ccccc1C2(CC=O)C(=O)CCCC2=O [O-][N+](=O)c1ccccc1C2(CC=O)C(=O)CCCC2=O 20 0 C[C@H](N1CC[C@]2([C@@H]1CCCC2=O)c3ccccc3[N+](=O)[O-])c4ccccc4 17.1.Bonjoch 18.Bonjoch C1CCC(CC1)C2CCCCC2 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C2CCCCC2 BonjochC1CCC(CC1)C23CCCCC2NCC3 15 0 18 18.1 13.72 72 2000 Bonjoch C[C@H](N1CC[C@]2([C@@H]1CCCC2=O)c3ccccc3[N+](=O)[O-])c4ccccc4 C[C@H](N1CC[C@]2([C@@H]1CCCC2=O)c3ccccc3[N+](=O)[O-])c4ccccc4 27 0 CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCCC2=O)c3ccccc3[N+](=O)[O-] 18.Bonjoch 18.1.Bonjoch C1CCC(CC1)C23CCCCC2NCC3 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 yes 15 0 18.1 18.2a 30.8 100 2000 Bonjoch CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCCC2=O)c3ccccc3[N+](=O)[O-] CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCCC2=O)c3ccccc3[N+](=O)[O-] 25 0 CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCC=C2O[Si](C)(C)C)c3ccccc3[N+](=O)[O-] 18.1.Bonjoch 18.2a.Bonjoch C1CCC(CC1)C23CCCCC2NCC3 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 yes 15 0 18.2a 18.2 12.7 70 2000 Bonjoch CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCC=C2O[Si](C)(C)C)c3ccccc3[N+](=O)[O-] CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCC=C2O[Si](C)(C)C)c3ccccc3[N+](=O)[O-] 29 0 CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCC([Se]c3ccccc3)C2=O)c4ccccc4[N+](=O)[O-] 18.2a.Bonjoch 18.2.Bonjoch C1CCC(CC1)C23CCCCC2NCC3 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 yes 15 0 18.2 18.3 8.87 72 2000 Bonjoch CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCC([Se]c3ccccc3)C2=O)c4ccccc4[N+](=O)[O-] CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CCC([Se]c3ccccc3)C2=O)c4ccccc4[N+](=O)[O-] 32 0 CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CC=CC2=O)c3ccccc3[N+](=O)[O-] 18.2.Bonjoch 18.3.Bonjoch C1CCC(CC1)C23CCCCC2NCC3 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 yes 15 0 18.3 18.4 6.39 100 2000 Bonjoch CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CC=CC2=O)c3ccccc3[N+](=O)[O-] CC(Cl)OC(=O)N1CC[C@]2([C@@H]1CC=CC2=O)c3ccccc3[N+](=O)[O-] 25 0 [O-][N+](=O)c1ccccc1[C@]23CCN[C@H]2CC=CC3=O 18.3.Bonjoch 18.4.Bonjoch C1CCC(CC1)C23CCCCC2NCC3 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 yes 15 0 18.4 11 1.36 74 2000 Bonjoch [O-][N+](=O)c1ccccc1[C@]23CCN[C@H]2CC=CC3=O [O-][N+](=O)c1ccccc1[C@]23CCN[C@H]2CC=CC3=O 19 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@]2([C@@H]1CC=CC2=O)c3ccccc3[N+](=O)[O-] 18.4.Bonjoch 11.Bonjoch C1CCC(CC1)C23CCCCC2NCC3 C1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCCCC2NCC3 yes 15 0 11 14 0.22 53 2000 Bonjoch CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@]2([C@@H]1CC=CC2=O)c3ccccc3[N+](=O)[O-] CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@]2([C@@H]1CC=CC2=O)c3ccccc3[N+](=O)[O-] 32 0 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@]3([C@@H]2C[C@@H]1CC3=O)c4ccccc4[N+](=O)[O-] 11.Bonjoch 14.Bonjoch C1CCC(CC1)C23CCCCC2NCC3 C1CCC(CC1)C23CCC4CCN(CC2)C3C4 BonjochC1CCC(CC1)C23CCCCC2NCC3 BonjochC1CCC(CC1)C23CCC4CCN(CC2)C3C4 yes 17 13 14 19 0.39 62 2000 Bonjoch CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@]3([C@@H]2C[C@@H]1CC3=O)c4ccccc4[N+](=O)[O-] CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@]3([C@@H]2C[C@@H]1CC3=O)c4ccccc4[N+](=O)[O-] 31 13 COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4[N+](=O)[O-] 14.Bonjoch 19.Bonjoch C1CCC(CC1)C23CCC4CCN(CC2)C3C4 C1CCC(CC1)C23CCC4CCN(CC2)C3C4 BonjochC1CCC(CC1)C23CCC4CCN(CC2)C3C4 BonjochC1CCC(CC1)C23CCC4CCN(CC2)C3C4 yes 17 13 14 14 8 2000 Bonjoch CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@]3([C@@H]2C[C@@H]1CC3=O)c4ccccc4[N+](=O)[O-] CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@]3([C@@H]2C[C@@H]1CC3=O)c4ccccc4[N+](=O)[O-] 31 13 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@]3([C@@H]2C[C@@H]1CC3=O)c4ccccc4[N+](=O)[O-] 14.Bonjoch 14.Bonjoch C1CCC(CC1)C23CCC4CCN(CC2)C3C4 C1CCC(CC1)C23CCC4CCN(CC2)C3C4 BonjochC1CCC(CC1)C23CCC4CCN(CC2)C3C4 BonjochC1CCC(CC1)C23CCC4CCN(CC2)C3C4 yes 17 13 19 21 0.37 3.3 2000 Bonjoch COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4[N+](=O)[O-] COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4[N+](=O)[O-] 35 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 19.Bonjoch 21.Bonjoch C1CCC(CC1)C23CCC4CCN(CC2)C3C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 BonjochC1CCC(CC1)C23CCC4CCN(CC2)C3C4 BonjochC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 17 13 19 20 0.37 32.7 2000 Bonjoch COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4[N+](=O)[O-] COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\CO[Si](C)(C)C(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4[N+](=O)[O-] 35 13 COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 19.Bonjoch 20.Bonjoch C1CCC(CC1)C23CCC4CCN(CC2)C3C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 BonjochC1CCC(CC1)C23CCC4CCN(CC2)C3C4 BonjochC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 20 21 0.13 72 2000 Bonjoch COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 25 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 20.Bonjoch 21.Bonjoch C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 BonjochC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 BonjochC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 21 Wieland-Gumlich aldhyde 0.12 65 2000 Bonjoch COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 25 13 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 21.Bonjoch Wieland-Gumlich aldhyde.Bonjoch C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 BonjochC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 BonjochC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 Wieland-Gumlich aldhyde Strychnine 49 2000 Bonjoch OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 Wieland-Gumlich aldhyde.Bonjoch Strychnine.Bonjoch C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 BonjochC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 BonjochC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 18 13 21 Strychnine 0.12 49 2000 Bonjoch COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 21.Bonjoch Strychnine.Bonjoch C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 BonjochC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 BonjochC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 24 25 Strychnine 2000 Bonjoch O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Bonjoch C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 BonjochC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . yes 5 0 28 29 140 97 1995 Overman CC(=O)O[C@@H]1C[C@H](O)C=C1 CC(=O)O[C@@H]1C[C@H](O)C=C1 10 0 COC(=O)O[C@H]1C[C@@H](OC(=O)C)C=C1 28.Overman 29.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 29 31 103 91 1995 Overman COC(=O)O[C@H]1C[C@@H](OC(=O)C)C=C1 COC(=O)O[C@H]1C[C@@H](OC(=O)C)C=C1 14 0 CCOC(=O)C([C@H]1C[C@@H](OC(=O)C)C=C1)C(=O)COC(C)(C)C 29.Overman 31.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 31 "32,33" 89.5 97 1995 Overman CCOC(=O)C([C@H]1C[C@@H](OC(=O)C)C=C1)C(=O)COC(C)(C)C CCOC(=O)C([C@H]1C[C@@H](OC(=O)C)C=C1)C(=O)COC(C)(C)C 23 0 CCOC(=O)C(C(O)COC(C)(C)C)[C@H]1C[C@@H](OC(=O)C)C=C1 31.Overman "32,33.Overman" C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 "32,33" 34 82 91 1995 Overman CCOC(=O)C(C(O)COC(C)(C)C)[C@H]1C[C@@H](OC(=O)C)C=C1 CCOC(=O)C(C(O)COC(C)(C)C)[C@H]1C[C@@H](OC(=O)C)C=C1 23 0 CCOC(=O)\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](OC(=O)C)C=C1 "32,33.Overman" 34.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 34 36 90 95 1995 Overman CCOC(=O)\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](OC(=O)C)C=C1 CCOC(=O)\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](OC(=O)C)C=C1 22 0 CC(C)(C)OC\C=C(\CO)/[C@H]1C[C@@H](O)C=C1 34.Overman 36.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 36 37 14 65 1995 Overman CC(C)(C)OC\C=C(\CO)/[C@H]1C[C@@H](O)C=C1 CC(C)(C)OC\C=C(\CO)/[C@H]1C[C@@H](O)C=C1 16 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](O)C=C1)(C(C)C)C(C)C 36.Overman 37.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 36 38 14 33 1995 Overman CC(C)(C)OC\C=C(\CO)/[C@H]1C[C@@H](O)C=C1 CC(C)(C)OC\C=C(\CO)/[C@H]1C[C@@H](O)C=C1 16 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](O[Si](C(C)C)(C(C)C)C(C)C)C=C1)(C(C)C)C(C)C 36.Overman 38.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 38 36 17 96 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](O[Si](C(C)C)(C(C)C)C(C)C)C=C1)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](O[Si](C(C)C)(C(C)C)C(C)C)C=C1)(C(C)C)C(C)C 36 0 CC(C)(C)OC\C=C(\CO)/[C@H]1C[C@@H](O)C=C1 38.Overman 36.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 37 9 7.2 98 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](O)C=C1)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@H]1C[C@@H](O)C=C1)(C(C)C)C(C)C 26 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CCC(=O)C1)(C(C)C)C(C)C 37.Overman 9.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 9 39 2.89 80 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CCC(=O)C1)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CCC(=O)C1)(C(C)C)C(C)C 26 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C 9.Overman 39.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 5 0 39 8 10.7 81 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C 33 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)[Sn](C)(C)C)(C(C)C)C(C)C 39.Overman 8.Overman C1CCCC1 C1CCCC1 OvermanC1CCCC1 OvermanC1CCCC1 yes 12 0 7 6 11.6 80 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2I CN1CN(CN(C)C1=O)c2ccccc2I 16 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)C(=O)c2ccccc2N3CN(C)C(=O)N(C)C3)(C(C)C)C(C)C 7.Overman 6.Overman C1CCC(CC1)N2CNCNC2 C(C1CCCC1)C2CCCCC2N3CNCNC3 OvermanC1CCC(CC1)N2CNCNC2 OvermanC(C1CCCC1)C2CCCCC2N3CNCNC3 5 0 8 6 11.4 80 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)[Sn](C)(C)C)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)[Sn](C)(C)C)(C(C)C)C(C)C 29 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)C(=O)c2ccccc2N3CN(C)C(=O)N(C)C3)(C(C)C)C(C)C 8.Overman 6.Overman C1CCCC1 C(C1CCCC1)C2CCCCC2N3CNCNC3 OvermanC1CCCC1 OvermanC(C1CCCC1)C2CCCCC2N3CNCNC3 yes 18 0 6 46 20.6 91 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)C(=O)c2ccccc2N3CN(C)C(=O)N(C)C3)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1CC=C(C1)C(=O)c2ccccc2N3CN(C)C(=O)N(C)C3)(C(C)C)C(C)C 42 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1C[C@H]2O[C@]2(C1)C(=O)c3ccccc3N4CN(C)C(=O)N(C)C4)(C(C)C)C(C)C 6.Overman 46.Overman C(C1CCCC1)C2CCCCC2N3CNCNC3 C(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCC1)C2CCCCC2N3CNCNC3 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 yes 19 0 46 47 17 92 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1C[C@H]2O[C@]2(C1)C(=O)c3ccccc3N4CN(C)C(=O)N(C)C4)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1C[C@H]2O[C@]2(C1)C(=O)c3ccccc3N4CN(C)C(=O)N(C)C4)(C(C)C)C(C)C 43 0 CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1C[C@H]2O[C@]2(C1)C(=C)c3ccccc3N4CN(C)C(=O)N(C)C4)(C(C)C)C(C)C 46.Overman 47.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 yes 19 0 47 48 14 97 1995 Overman CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1C[C@H]2O[C@]2(C1)C(=C)c3ccccc3N4CN(C)C(=O)N(C)C4)(C(C)C)C(C)C CC(C)[Si](OC\C(=C\COC(C)(C)C)\[C@@H]1C[C@H]2O[C@]2(C1)C(=C)c3ccccc3N4CN(C)C(=O)N(C)C4)(C(C)C)C(C)C 43 0 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CO 47.Overman 48.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 yes 19 0 48 48.1 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CO CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CO 33 0 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\COS(=O)(=O)C 48.Overman 48.1.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 ND yes 19 0 48.1 49 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\COS(=O)(=O)C CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\COS(=O)(=O)C 37 0 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CCl 48.1.Overman 49.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 yes 19 0 49 50 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CCl CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CCl 33 0 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CNC(=O)C(F)(F)F 49.Overman 50.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 yes 19 0 48 50 14 75 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CO CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CO 33 0 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CNC(=O)C(F)(F)F 48.Overman 50.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 yes 19 0 50 51 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CNC(=O)C(F)(F)F CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CNC(=O)C(F)(F)F 39 0 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]3(O)C[C@H]4C[C@@H]3N(C/C/4=C\COC(C)(C)C)C(=O)C(F)(F)F 50.Overman 51.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 135.5-7 yes 21 9 51 5 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]3(O)C[C@H]4C[C@@H]3N(C/C/4=C\COC(C)(C)C)C(=O)C(F)(F)F CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]3(O)C[C@H]4C[C@@H]3N(C/C/4=C\COC(C)(C)C)C(=O)C(F)(F)F 39 9 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]3(O)C[C@H]4C[C@@H]3NC/C/4=C\COC(C)(C)C 51.Overman 5.Overman C(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 C(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 OvermanC(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 OvermanC(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 yes 19 0 50 5 5.4 75 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CNC(=O)C(F)(F)F CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]34C[C@@H](C[C@H]3O4)\C(=C/COC(C)(C)C)\CNC(=O)C(F)(F)F 39 0 CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]3(O)C[C@H]4C[C@@H]3NC/C/4=C\COC(C)(C)C 50.Overman 5.Overman C(C1CCCCC1N2CNCNC2)C34CCCC3O4 C(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 OvermanC(C1CCCCC1N2CNCNC2)C34CCCC3O4 OvermanC(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 yes 21 9 5 4 3.5 98 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]3(O)C[C@H]4C[C@@H]3NC/C/4=C\COC(C)(C)C CN1CN(CN(C)C1=O)c2ccccc2C(=C)[C@]3(O)C[C@H]4C[C@@H]3NC/C/4=C\COC(C)(C)C 33 9 CN1CN(CN(C)C1=O)c2ccccc2[C@]34CCN5C\C(=C\COC(C)(C)C)\[C@H](C[C@@H]35)CC4=O 5.Overman 4.Overman C(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 C1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 OvermanC(C1CCCCC1N2CNCNC2)C3CC4CCNC3C4 OvermanC1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 144-5 yes 23 13 4 52 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2[C@]34CCN5C\C(=C\COC(C)(C)C)\[C@H](C[C@@H]35)CC4=O CN1CN(CN(C)C1=O)c2ccccc2[C@]34CCN5C\C(=C\COC(C)(C)C)\[C@H](C[C@@H]35)CC4=O 34 13 COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\COC(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4N5CN(C)C(=O)N(C)C5 4.Overman 52.Overman C1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 C1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 OvermanC1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 OvermanC1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 151-2 yes 23 13 52 3 1995 Overman COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\COC(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4N5CN(C)C(=O)N(C)C5 COC(=O)C1=C(O)[C@]2(CCN3C\C(=C\COC(C)(C)C)\[C@@H]1C[C@@H]23)c4ccccc4N5CN(C)C(=O)N(C)C5 38 13 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 52.Overman 3.Overman C1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 23 13 4 3 3.4 70 1995 Overman CN1CN(CN(C)C1=O)c2ccccc2[C@]34CCN5C\C(=C\COC(C)(C)C)\[C@H](C[C@@H]35)CC4=O CN1CN(CN(C)C1=O)c2ccccc2[C@]34CCN5C\C(=C\COC(C)(C)C)\[C@H](C[C@@H]35)CC4=O 34 13 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 4.Overman 3.Overman C1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC(C(C1)N2CNCNC2)C34CCC5CCN(CC3)C4C5 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 3 53 1995 Overman COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 25 13 COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 3.Overman 53.Overman C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 53 54 1995 Overman COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 25 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 53.Overman 54.Overman C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 3 54 2.4 68 1995 Overman COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C\C(=C\CO)\[C@@H]1C[C@@H]45 25 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 3.Overman 54.Overman C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 54 2 1995 Overman COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 25 13 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 54.Overman 2.Overman C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 278-85 yes 22 18 2 Strychnine 1995 Overman OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 2.Overman Strychnine.Overman C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 OvermanC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 OvermanC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 18 13 54 Strychnine 0.012 51 1995 Overman COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C/C/2=C/CO 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 54.Overman Strychnine.Overman C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 OvermanC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 OvermanC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 24 25 Strychnine 1995 Overman O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Overman C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 OvermanC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . 278-85 yes 6 0 1 3 114 79 1994 Rawal [O-][N+](=O)c1ccccc1CC#N [O-][N+](=O)c1ccccc1CC#N 12 0 COC(=O)N1CCC(=C1)c2ccccc2N 1.Rawal 3.Rawal C1CCCCC1 C1CCC(CC1)C2CCNC2 RawalC1CCCCC1 RawalC1CCC(CC1)C2CCNC2 6 0 1 1.1 1994 Rawal [O-][N+](=O)c1ccccc1CC#N [O-][N+](=O)c1ccccc1CC#N 12 0 [O-][N+](=O)c1ccccc1C2(CC2)C#N 1.Rawal 1.1.Rawal C1CCCCC1 C1CCC(CC1)C2CC2 RawalC1CCCCC1 RawalC1CCC(CC1)C2CC2 9 0 1.1 1.2 1994 Rawal [O-][N+](=O)c1ccccc1C2(CC2)C#N [O-][N+](=O)c1ccccc1C2(CC2)C#N 14 0 [O-][N+](=O)c1ccccc1C2(CC2)C=O 1.1.Rawal 1.2.Rawal C1CCC(CC1)C2CC2 C1CCC(CC1)C2CC2 RawalC1CCC(CC1)C2CC2 RawalC1CCC(CC1)C2CC2 6 0 1 1.2 96 1994 Rawal [O-][N+](=O)c1ccccc1CC#N [O-][N+](=O)c1ccccc1CC#N 12 0 [O-][N+](=O)c1ccccc1C2(CC2)C=O 1.Rawal 1.2.Rawal C1CCCCC1 C1CCC(CC1)C2CC2 RawalC1CCCCC1 RawalC1CCC(CC1)C2CC2 9 0 1.2 1.3 1994 Rawal [O-][N+](=O)c1ccccc1C2(CC2)C=O [O-][N+](=O)c1ccccc1C2(CC2)C=O 14 0 [O-][N+](=O)c1ccccc1C2(CC2)\C=N\Cc3ccccc3 1.2.Rawal 1.3.Rawal C1CCC(CC1)C2CC2 C1CCC(CC1)C2CC2 RawalC1CCC(CC1)C2CC2 RawalC1CCC(CC1)C2CC2 9 0 1.3 1.4 1994 Rawal [O-][N+](=O)c1ccccc1C2(CC2)\C=N\Cc3ccccc3 [O-][N+](=O)c1ccccc1C2(CC2)\C=N\Cc3ccccc3 21 0 [O-][N+](=O)c1ccccc1C2=CN(Cc3ccccc3)CC2 1.3.Rawal 1.4.Rawal C1CCC(CC1)C2CC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CC2 RawalC1CCC(CC1)C2CCNC2 9 0 1.2 1.4 96 1994 Rawal [O-][N+](=O)c1ccccc1C2(CC2)C=O [O-][N+](=O)c1ccccc1C2(CC2)C=O 14 0 [O-][N+](=O)c1ccccc1C2=CN(Cc3ccccc3)CC2 1.2.Rawal 1.4.Rawal C1CCC(CC1)C2CC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CC2 RawalC1CCC(CC1)C2CCNC2 11 0 1.4 1.5 1994 Rawal [O-][N+](=O)c1ccccc1C2=CN(Cc3ccccc3)CC2 [O-][N+](=O)c1ccccc1C2=CN(Cc3ccccc3)CC2 21 0 COC(=O)N1CCC(=C1)c2ccccc2[N+](=O)[O-] 1.4.Rawal 1.5.Rawal C1CCC(CC1)C2CCNC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 11 0 1.5 3 1994 Rawal COC(=O)N1CCC(=C1)c2ccccc2[N+](=O)[O-] COC(=O)N1CCC(=C1)c2ccccc2[N+](=O)[O-] 18 0 COC(=O)N1CCC(=C1)c2ccccc2N 1.5.Rawal 3.Rawal C1CCC(CC1)C2CCNC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 11 0 1.4 3 86 1994 Rawal [O-][N+](=O)c1ccccc1C2=CN(Cc3ccccc3)CC2 [O-][N+](=O)c1ccccc1C2=CN(Cc3ccccc3)CC2 21 0 COC(=O)N1CCC(=C1)c2ccccc2N 1.4.Rawal 3.Rawal C1CCC(CC1)C2CCNC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 11 0 3 3.1 2.04 99 1994 Rawal COC(=O)N1CCC(=C1)c2ccccc2N COC(=O)N1CCC(=C1)c2ccccc2N 16 0 COC(=O)CC\C(=C/Nc1ccccc1C2=CN(CC2)C(=O)OC)\C=C 3.Rawal 3.1.Rawal C1CCC(CC1)C2CCNC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 11 0 3.1 5 2 85 1994 Rawal COC(=O)CC\C(=C/Nc1ccccc1C2=CN(CC2)C(=O)OC)\C=C COC(=O)CC\C(=C/Nc1ccccc1C2=CN(CC2)C(=O)OC)\C=C 26 0 COC(=O)CC\C(=C/N(C(=O)OC)c1ccccc1C2=CN(CC2)C(=O)OC)\C=C 3.1.Rawal 5.Rawal C1CCC(CC1)C2CCNC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 11 0 3 3.1 2.04 99 1994 Rawal COC(=O)N1CCC(=C1)c2ccccc2N COC(=O)N1CCC(=C1)c2ccccc2N 16 0 COC(=O)CC\C(=C/Nc1ccccc1C2=CN(CC2)C(=O)OC)\C=C 3.Rawal 3.1.Rawal C1CCC(CC1)C2CCNC2 C1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 RawalC1CCC(CC1)C2CCNC2 11 0 5 6 0.48 99 1994 Rawal COC(=O)CC\C(=C/N(C(=O)OC)c1ccccc1C2=CN(CC2)C(=O)OC)\C=C COC(=O)CC\C(=C/N(C(=O)OC)c1ccccc1C2=CN(CC2)C(=O)OC)\C=C 30 0 COC(=O)CCC1=CC[C@@H]2N(CC[C@]23[C@H]1N(C(=O)OC)c4ccccc34)C(=O)OC 5.Rawal 6.Rawal C1CCC(CC1)C2CCNC2 C1CCC2C(C1)NC3CCCC4NCCC234 RawalC1CCC(CC1)C2CCNC2 RawalC1CCC2C(C1)NC3CCCC4NCCC234 16 0 6 7 0.082 90 1994 Rawal COC(=O)CCC1=CC[C@@H]2N(CC[C@]23[C@H]1N(C(=O)OC)c4ccccc34)C(=O)OC COC(=O)CCC1=CC[C@@H]2N(CC[C@]23[C@H]1N(C(=O)OC)c4ccccc34)C(=O)OC 30 0 O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 6.Rawal 7.Rawal C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 RawalC1CCC2C(C1)NC3CCCC4NCCC234 RawalC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 7 9 0.38 75 1994 Rawal O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 20 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 7.Rawal 9.Rawal C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 RawalC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 RawalC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 9 9.1 0.18 74 1994 Rawal CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 33 0 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 9.Rawal 9.1.Rawal C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 RawalC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 RawalC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 9.1 10 0.49 91 1994 Rawal CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 32 13 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 9.1.Rawal 10.Rawal C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 RawalC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 RawalC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 10 Strychnine 1.05 10 1994 Rawal OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 10.Rawal Strychnine.Rawal C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 RawalC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 RawalC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 no 24 25 Strychnine 1994 Rawal O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Rawal C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 RawalC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . no 9 0 tryptamine A18 188 89 1993 Kuehne NCCc1c[nH]c2c(H)cccc12 NCCc1c[nH]c2ccccc12 12 0 C(Cc1c[nH]c2ccccc12)N(Cc3ccccc3)Cc4ccccc4 tryptamine.Kuehne A18.Kuehne C1CCC2NCCC2C1 C1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 9 0 A18 A20 88.2 83 1993 Kuehne C(Cc1c[nH]c2ccccc12)N(Cc3ccccc3)Cc4ccccc4 C(Cc1c[nH]c2ccccc12)N(Cc3ccccc3)Cc4ccccc4 26 0 COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCN(Cc3ccccc3)Cc4ccccc4 A18.Kuehne A20.Kuehne C1CCC2NCCC2C1 C1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 9 0 A18 A19 1993 Kuehne C(Cc1c[nH]c2ccccc12)N(Cc3ccccc3)Cc4ccccc4 C(Cc1c[nH]c2ccccc12)N(Cc3ccccc3)Cc4ccccc4 26 0 ClC1(CCN(Cc2ccccc2)Cc3ccccc3)C=Nc4ccccc14 A18.Kuehne A19.Kuehne C1CCC2NCCC2C1 C1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 9 0 A19 A20 1993 Kuehne ClC1(CCN(Cc2ccccc2)Cc3ccccc3)C=Nc4ccccc14 ClC1(CCN(Cc2ccccc2)Cc3ccccc3)C=Nc4ccccc14 27 0 COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCN(Cc3ccccc3)Cc4ccccc4 A19.Kuehne A20.Kuehne C1CCC2NCCC2C1 C1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 9 0 A20 A20.1 4.3 84 1993 Kuehne COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCN(Cc3ccccc3)Cc4ccccc4 COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCN(Cc3ccccc3)Cc4ccccc4 35 0 COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCNCc3ccccc3 A20.Kuehne A20.1.Kuehne C1CCC2NCCC2C1 C1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 104 9 0 A20.1 3 6.94 84 1993 Kuehne COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCNCc3ccccc3 COC(=O)C(C(=O)OC)c1[nH]c2ccccc2c1CCNCc3ccccc3 28 0 COC(=O)Cc1[nH]c2ccccc2c1CCNCc3ccccc3 A20.1.Kuehne 3.Kuehne C1CCC2NCCC2C1 C1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 KuehneC1CCC2NCCC2C1 9 0 3 2 1993 Kuehne COC(=O)Cc1[nH]c2ccccc2c1CCNCc3ccccc3 COC(=O)Cc1[nH]c2ccccc2c1CCNCc3ccccc3 24 0 COC(OC)[C@@H]1C[C@@H]2N(Cc3ccccc3)CC[C@]24C(=C1C(=O)OC)Nc5ccccc45 3.Kuehne 2.Kuehne C1CCC2NCCC2C1 C1CCC2C(C1)NC3CCCC4NCCC234 KuehneC1CCC2NCCC2C1 KuehneC1CCC2C(C1)NC3CCCC4NCCC234 81-3 9 0 3 7 30.9 51 1993 Kuehne COC(=O)Cc1[nH]c2ccccc2c1CCNCc3ccccc3 COC(=O)Cc1[nH]c2ccccc2c1CCNCc3ccccc3 24 0 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN(Cc5ccccc5)[C@H]4C[C@H]1C=O 3.Kuehne 7.Kuehne C1CCC2NCCC2C1 C1CCC2C(C1)NC3CCCC4NCCC234 KuehneC1CCC2NCCC2C1 KuehneC1CCC2C(C1)NC3CCCC4NCCC234 81-3 16 0 2 7 1993 Kuehne COC(OC)[C@@H]1C[C@@H]2N(Cc3ccccc3)CC[C@]24C(=C1C(=O)OC)Nc5ccccc45 COC(OC)[C@@H]1C[C@@H]2N(Cc3ccccc3)CC[C@]24C(=C1C(=O)OC)Nc5ccccc45 32 0 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN(Cc5ccccc5)[C@H]4C[C@H]1C=O 2.Kuehne 7.Kuehne C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CCCC4NCCC234 KuehneC1CCC2C(C1)NC3CCCC4NCCC234 KuehneC1CCC2C(C1)NC3CCCC4NCCC234 no 16 0 7 9a 1993 Kuehne COC(=O)C1=C2Nc3ccccc3[C@@]24CCN(Cc5ccccc5)[C@H]4C[C@H]1C=O COC(=O)C1=C2Nc3ccccc3[C@@]24CCN(Cc5ccccc5)[C@H]4C[C@H]1C=O 29 0 COC(=O)C1=C2Nc3ccccc3[C@@]24CC[N+]5(Cc6ccccc6)[C@H](CO)[C@@H]1C[C@@H]45 7.Kuehne 9a.Kuehne C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CC4CC5N(CCC235)C4 KuehneC1CCC2C(C1)NC3CCCC4NCCC234 KuehneC1CCC2C(C1)NC3CC4CC5N(CCC235)C4 83-5 no 17 12 9a 9b 1993 Kuehne COC(=O)C1=C2Nc3ccccc3[C@@]24CC[N+]5(Cc6ccccc6)[C@H](CO)[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CC[N+]5(Cc6ccccc6)[C@H](CO)[C@@H]1C[C@@H]45 30 12 COC(=O)C1=C2Nc3ccccc3[C@@]24CC[N+]5(Cc6ccccc6)C[C@H](O)[C@@H]1C[C@@H]45 9a.Kuehne 9b.Kuehne C1CCC2C(C1)NC3CC4CC5N(CCC235)C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CC5N(CCC235)C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 9b 11 1993 Kuehne COC(=O)C1=C2Nc3ccccc3[C@@]24CC[N+]5(Cc6ccccc6)C[C@H](O)[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CC[N+]5(Cc6ccccc6)C[C@H](O)[C@@H]1C[C@@H]45 30 13 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C[C@H](O)[C@@H]1C[C@@H]45 9b.Kuehne 11.Kuehne C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 16 0 7 11 8.54 70 1993 Kuehne COC(=O)C1=C2Nc3ccccc3[C@@]24CCN(Cc5ccccc5)[C@H]4C[C@H]1C=O COC(=O)C1=C2Nc3ccccc3[C@@]24CCN(Cc5ccccc5)[C@H]4C[C@H]1C=O 29 0 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C[C@H](O)[C@@H]1C[C@@H]45 7.Kuehne 11.Kuehne C1CCC2C(C1)NC3CCCC4NCCC234 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CCCC4NCCC234 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 83-5 no 18 13 11 12 6.4 83 1993 Kuehne COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C[C@H](O)[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C[C@H](O)[C@@H]1C[C@@H]45 23 13 COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2O 11.Kuehne 12.Kuehne C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 214-5 no 18 13 11 11.1 1993 Kuehne COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C[C@H](O)[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5C[C@H](O)[C@@H]1C[C@@H]45 23 13 COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C[C@@H]2O 11.Kuehne 11.1.Kuehne C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 214-5 no 18 13 11.1 11.2 1993 Kuehne COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C[C@@H]2O COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)C[C@@H]2O 23 13 COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2OC(=O)C 11.1.Kuehne 11.2.Kuehne C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 11.2 12 1993 Kuehne COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2OC(=O)C COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2OC(=O)C 29 13 COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2O 11.2.Kuehne 12.Kuehne C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 12 16 1993 Kuehne COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2O COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2O 26 13 O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5[C@@H]3N(C(=O)CC5=O)c6ccccc46 12.Kuehne 16.Kuehne C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 248-50 no 21 13 16 16.1 1993 Kuehne O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5[C@@H]3N(C(=O)CC5=O)c6ccccc46 O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5[C@@H]3N(C(=O)CC5=O)c6ccccc46 24 13 O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5C(O)CC(=O)N([C@H]35)c6ccccc46 16.Kuehne 16.1.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 18 13 12 16.1 0.14 64 1993 Kuehne COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2O COC(=O)C1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(C(=O)C)c5ccccc45)C[C@@H]2O 26 13 O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5C(O)CC(=O)N([C@H]35)c6ccccc46 12.Kuehne 16.1.Kuehne C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 248-50 no 21 13 16.1 "17,18" 0.062 98 1993 Kuehne O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5C(O)CC(=O)N([C@H]35)c6ccccc46 O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5C(O)CC(=O)N([C@H]35)c6ccccc46 24 13 CC(=O)O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5C(CC(=O)N([C@H]35)c6ccccc46)OC(=O)C 16.1.Kuehne "17,18.Kuehne" C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 "17,18" 19 0.877 61 1993 Kuehne CC(=O)O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5C(CC(=O)N([C@H]35)c6ccccc46)OC(=O)C CC(=O)O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5C(CC(=O)N([C@H]35)c6ccccc46)OC(=O)C 30 13 O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 "17,18.Kuehne" 19.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 19 20 0.065 98 1993 Kuehne O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 O[C@H]1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 23 13 O=C1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 19.Kuehne 20.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 219-20 no 21 13 20 21 0.72 40.5 1993 Kuehne O=C1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 O=C1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 23 13 COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 20.Kuehne 21.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 20 22 0.72 40.5 1993 Kuehne O=C1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 O=C1CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 23 13 COC(=O)\C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 20.Kuehne 22.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 21 23 0.055 87 1993 Kuehne COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 27 13 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 21.Kuehne 23.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 22 21 0.138 76 1993 Kuehne COC(=O)\C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 COC(=O)\C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 27 13 COC(=O)\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 22.Kuehne 21.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 23 Strychnine 0.33 28 1993 Kuehne OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 23.Kuehne Strychnine.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 ND no 21 13 23 23 61 1993 Kuehne OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 25 13 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 23.Kuehne 23.Kuehne C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 KuehneC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 24 25 Strychnine 1993 Kuehne O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Kuehne C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 KuehneC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . no 9 0 tryptamine 9a 1992 Magnus NCCc1c[nH]c2cc(H)ccc12 NCCc1c[nH]c2ccccc12 12 0 COC(=O)C12CCC(=O)N1CCc3c2[nH]c4ccccc34 tryptamine.Magnus 9a.Magnus C1CCC2NCCC2C1 C1CCC2C(C1)NC3C2CCN4CCCC34 MagnusC1CCC2NCCC2C1 MagnusC1CCC2C(C1)NC3C2CCN4CCCC34 16 0 9a 9b 1.29 83 1992 Magnus COC(=O)C12CCC(=O)N1CCc3c2[nH]c4ccccc34 COC(=O)C12CCC(=O)N1CCc3c2[nH]c4ccccc34 21 0 COC(=O)C12CCC(=S)N1CCc3c2[nH]c4ccccc34 9a.Magnus 9b.Magnus C1CCC2C(C1)NC3C2CCN4CCCC34 C1CCC2C(C1)NC3C2CCN4CCCC34 MagnusC1CCC2C(C1)NC3C2CCN4CCCC34 MagnusC1CCC2C(C1)NC3C2CCN4CCCC34 no 16 0 9b 9 3.02 97 1992 Magnus COC(=O)C12CCC(=S)N1CCc3c2[nH]c4ccccc34 COC(=O)C12CCC(=S)N1CCc3c2[nH]c4ccccc34 21 0 COC(=O)C12CCCN1CCc3c2[nH]c4ccccc34 9b.Magnus 9.Magnus C1CCC2C(C1)NC3C2CCN4CCCC34 C1CCC2C(C1)NC3C2CCN4CCCC34 MagnusC1CCC2C(C1)NC3C2CCN4CCCC34 MagnusC1CCC2C(C1)NC3C2CCN4CCCC34 no 16 0 9 10 11 79.2 1992 Magnus COC(=O)C12CCCN1CCc3c2[nH]c4ccccc34 COC(=O)C12CCCN1CCc3c2[nH]c4ccccc34 20 0 COC(=O)C1(Cl)CCCN(CCc2c1[nH]c3ccccc23)C(=O)OCC(Cl)(Cl)Cl 9.Magnus 10.Magnus C1CCC2C(C1)NC3C2CCN4CCCC34 C1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2C(C1)NC3C2CCN4CCCC34 MagnusC1CCC2NC3CCCCC3C2CCNC1 no 16 0 9 11 11 10 1992 Magnus COC(=O)C12CCCN1CCc3c2[nH]c4ccccc34 COC(=O)C12CCCN1CCc3c2[nH]c4ccccc34 20 0 COC(=O)\C\1=C\CCN(CCc2c1[nH]c3ccccc23)C(=O)OCC(Cl)(Cl)Cl 9.Magnus 11.Magnus C1CCC2C(C1)NC3C2CCN4CCCC34 C1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2C(C1)NC3C2CCN4CCCC34 MagnusC1CCC2NC3CCCCC3C2CCNC1 no 16 0 10 11 28 98.5 1992 Magnus COC(=O)C1(Cl)CCCN(CCc2c1[nH]c3ccccc23)C(=O)OCC(Cl)(Cl)Cl COC(=O)C1(Cl)CCCN(CCc2c1[nH]c3ccccc23)C(=O)OCC(Cl)(Cl)Cl 29 0 COC(=O)\C\1=C\CCN(CCc2c1[nH]c3ccccc23)C(=O)OCC(Cl)(Cl)Cl 10.Magnus 11.Magnus C1CCC2NC3CCCCC3C2CCNC1 C1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 no 16 0 11 12 16.6 86 1992 Magnus COC(=O)\C\1=C\CCN(CCc2c1[nH]c3ccccc23)C(=O)OCC(Cl)(Cl)Cl COC(=O)\C\1=C\CCN(CCc2c1[nH]c3ccccc23)C(=O)OCC(Cl)(Cl)Cl 28 0 COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)OCC(Cl)(Cl)Cl 11.Magnus 12.Magnus C1CCC2NC3CCCCC3C2CCNC1 C1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 16 0 12 13 3.97 82.2 1992 Magnus COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)OCC(Cl)(Cl)Cl COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)OCC(Cl)(Cl)Cl 32 0 COC(=O)\C\1=C\CCNCCc2c1n(C(=O)OC)c3ccccc23 12.Magnus 13.Magnus C1CCC2NC3CCCCC3C2CCNC1 C1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 16 0 13 15 38.1 71 1992 Magnus COC(=O)\C\1=C\CCNCCc2c1n(C(=O)OC)c3ccccc23 COC(=O)\C\1=C\CCNCCc2c1n(C(=O)OC)c3ccccc23 24 0 COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)CSc4ccccc4 13.Magnus 15.Magnus C1CCC2NC3CCCCC3C2CCNC1 C1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 16 0 15 18 1.05 95 1992 Magnus COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)CSc4ccccc4 COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)CSc4ccccc4 34 0 COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)C[S+]([O-])c4ccccc4 15.Magnus 18.Magnus C1CCC2NC3CCCCC3C2CCNC1 C1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2NC3CCCCC3C2CCNC1 16 0 18 19 10.12 98 1992 Magnus COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)C[S+]([O-])c4ccccc4 COC(=O)\C\1=C\CCN(CCc2c1n(C(=O)OC)c3ccccc23)C(=O)C[S+]([O-])c4ccccc4 35 0 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@H]2[S+]([O-])c5ccccc5 18.Magnus 19.Magnus C1CCC2NC3CCCCC3C2CCNC1 C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2NC3CCCCC3C2CCNC1 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 no 18 12 19 26 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@H]2[S+]([O-])c5ccccc5 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@H]2[S+]([O-])c5ccccc5 35 12 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@@]2(OC(=O)C(F)(F)F)Sc5ccccc5 19.Magnus 26.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 no 18 12 26 27 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@@]2(OC(=O)C(F)(F)F)Sc5ccccc5 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@@]2(OC(=O)C(F)(F)F)Sc5ccccc5 41 12 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)C2=O 26.Magnus 27.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 187-90 no 18 12 27 33 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)C2=O COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)C2=O 28 12 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)C25OCCO5 27.Magnus 33.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 109-11 no 18 12 19 33 20.7 81 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@H]2[S+]([O-])c5ccccc5 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)[C@H]2[S+]([O-])c5ccccc5 35 12 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)C25OCCO5 19.Magnus 33.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 no 18 12 33 34 1.167 100 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)C25OCCO5 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)C(=O)C25OCCO5 31 12 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)CC25OCCO5 33.Magnus 34.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 215-6 no 18 12 34 35 10.86 71.9 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)CC25OCCO5 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)CC25OCCO5 30 12 COC(=O)[C@H]1[C@H]2CCN(CCc3c1[nH]c4ccccc34)CC25OCCO5 34.Magnus 35.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 no 18 12 34 36 10.86 10.8 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)CC25OCCO5 COC(=O)[C@H]1[C@H]2CCN(CCc3c1n(C(=O)OC)c4ccccc34)CC25OCCO5 30 12 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5CC6(OCCO6)[C@@H]1C[C@@H]45 34.Magnus 36.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 12 35 36 1.18 46 1992 Magnus COC(=O)[C@H]1[C@H]2CCN(CCc3c1[nH]c4ccccc34)CC25OCCO5 COC(=O)[C@H]1[C@H]2CCN(CCc3c1[nH]c4ccccc34)CC25OCCO5 26 12 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5CC6(OCCO6)[C@@H]1C[C@@H]45 35.Magnus 36.Magnus C1CCC2C(C1)NC3CC4CCN(CC4)CCC23 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN(CC4)CCC23 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 36 39 3.53 88.2 1992 Magnus COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5CC6(OCCO6)[C@@H]1C[C@@H]45 COC(=O)C1=C2Nc3ccccc3[C@@]24CCN5CC6(OCCO6)[C@@H]1C[C@@H]45 26 13 COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)CC26OCCO6 36.Magnus 39.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 190-5 no 18 13 39 40 0.21 100 1992 Magnus COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)CC26OCCO6 COC(=O)[C@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)CC26OCCO6 26 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)CC26OCCO6 39.Magnus 40.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 40 44 0.28 81 1992 Magnus COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)CC26OCCO6 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1Nc5ccccc45)CC26OCCO6 26 13 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(c5ccccc45)S(=O)(=O)c6ccc(OC)cc6)CC27OCCO7 40.Magnus 44.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 44 45 0.161 67 1992 Magnus COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(c5ccccc45)S(=O)(=O)c6ccc(OC)cc6)CC27OCCO7 COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@]34[C@H]1N(c5ccccc45)S(=O)(=O)c6ccc(OC)cc6)CC27OCCO7 37 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC47OCCO7 44.Magnus 45.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 no 18 13 45 47 0.2 55 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC47OCCO7 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC47OCCO7 35 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4COC5(O)CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 45.Magnus 47.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3C4COC5CN6CCC23C6CC45 no 22 18 48 49 25 97 1992 Magnus OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 48.Magnus 49.Magnus C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 49 50 17 72 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 34 18 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)O[C@H](CO)[C@]5(O)CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 49.Magnus 50.Magnus C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3C4COCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3C4COCC5CN6CCC23C6CC45 178-82 yes 21 17 50 51 9.72 56 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)O[C@H](CO)[C@]5(O)CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)O[C@H](CO)[C@]5(O)CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 36 17 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C[C@@]4(O)[C@H](O)CO 50.Magnus 51.Magnus C1CCC2C(C1)NC3C4COCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3C4COCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 257-9 yes 18 13 51 47 11.05 40 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C[C@@]4(O)[C@H](O)CO COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C[C@@]4(O)[C@H](O)CO 36 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4COC5(O)CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 51.Magnus 47.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3C4COC5CN6CCC23C6CC45 yes 20 16 47 52 0.319 69 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4COC5(O)CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4COC5(O)CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 32 16 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O 47.Magnus 52.Magnus C1CCC2C(C1)NC3C4COC5CN6CCC23C6CC45 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3C4COC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 52 53 2 43 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O 42 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C#N 52.Magnus 53.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 52 54 2 29 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O 42 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C\C#N 52.Magnus 54.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 52 52 12.5 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O 42 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)CC4=O 52.Magnus 52.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 54 53 0.047 40 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C\C#N COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C\C#N 44 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C#N 54.Magnus 53.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 53 53.1 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C#N COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C#N 44 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C=O 53.Magnus 53.1.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 239-41 yes 18 13 53.1 55 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C=O COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C=O 44 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO 53.1.Magnus 55.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 53 55 0.79 31 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C#N COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/C#N 44 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO 53.Magnus 55.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 22 18 49 56 1 90 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 34 18 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO 49.Magnus 56.Magnus C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 yes 18 13 55 56 0.14 81 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO[Si](C(C)C)(C(C)C)C(C)C)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO 44 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO 55.Magnus 56.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 250-1 yes 18 13 56 57 0.1 60 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO 34 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO[Si](C(C)C)(C(C)C)C(C)C 56.Magnus 57.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 244-5 yes 18 13 57 58 0.355 70 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO[Si](C(C)C)(C(C)C)C(C)C COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](CO)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO[Si](C(C)C)(C(C)C)C(C)C 44 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](C=O)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO[Si](C(C)C)(C(C)C)C(C)C 57.Magnus 58.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 173-2 yes 18 13 58 49 0.033 60 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](C=O)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO[Si](C(C)C)(C(C)C)C(C)C COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@H](C=O)[C@H]4C[C@@H]5N(CC[C@]35c6ccccc26)C/C/4=C/CO[Si](C(C)C)(C(C)C)C(C)C 44 13 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 58.Magnus 49.Magnus C1CCC2C(C1)NC3CC4CCN5CCC23C5C4 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3CC4CCN5CCC23C5C4 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 49 48 0.24 90 1992 Magnus COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 COc1ccc(cc1)S(=O)(=O)N2[C@H]3[C@@H]4C(O)OCC=C5CN6CC[C@]3([C@@H]6C[C@H]45)c7ccccc27 34 18 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 49.Magnus 48.Magnus C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 yes 22 18 48 Strychnine 0.65 70 1992 Magnus OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 OC1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4Nc6ccccc56 23 18 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 48.Magnus Strychnine.Magnus C1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 MagnusC1CCC2C(C1)NC3C4COCCC5CN6CCC23C6CC45 MagnusC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 24 25 Strychnine 1992 Magnus O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 Strychnine.Magnus C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 MagnusC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 . yes 6 0 Acetoveratrone II 138.8 54.4 1954 Woodward COc1ccc(cc1OC)C(=O)C COc1ccc(cc1OC)C(=O)C 13 0 COc1ccc(cc1OC)c2cc3ccccc3[nH]2 Acetoveratrone.Woodward II.Woodward C1CCCCC1 C1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCCCC1 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 15 0 II VI-NME2 22.1 92 1954 Woodward COc1ccc(cc1OC)c2cc3ccccc3[nH]2 COc1ccc(cc1OC)c2cc3ccccc3[nH]2 19 0 COc1ccc(cc1OC)c2[nH]c3ccccc3c2CN(C)C II.Woodward VI-NME2.Woodward C1CCC(CC1)C2CC3CCCCC3N2 C1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 185-9 15 0 VI-NME2 VI-NME3 20.3 100 1954 Woodward COc1ccc(cc1OC)c2[nH]c3ccccc3c2CN(C)C COc1ccc(cc1OC)c2[nH]c3ccccc3c2CN(C)C 23 0 COc1ccc(cc1OC)c2[nH]c3ccccc3c2C[N+](C)(C)C VI-NME2.Woodward VI-NME3.Woodward C1CCC(CC1)C2CC3CCCCC3N2 C1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 122-4 15 0 VI-NME3 VI-CN 20.3 97 1954 Woodward COc1ccc(cc1OC)c2[nH]c3ccccc3c2C[N+](C)(C)C COc1ccc(cc1OC)c2[nH]c3ccccc3c2C[N+](C)(C)C 24 0 COc1ccc(cc1OC)c2[nH]c3ccccc3c2CC#N VI-NME3.Woodward VI-CN.Woodward C1CCC(CC1)C2CC3CCCCC3N2 C1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 15 0 VI-CN V 342 85 1954 Woodward COc1ccc(cc1OC)c2[nH]c3ccccc3c2CC#N COc1ccc(cc1OC)c2[nH]c3ccccc3c2CC#N 22 0 COc1ccc(cc1OC)c2[nH]c3ccccc3c2CCN VI-CN.Woodward V.Woodward C1CCC(CC1)C2CC3CCCCC3N2 C1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 231-4 15 0 V VII 327 92 1954 Woodward COc1ccc(cc1OC)c2[nH]c3ccccc3c2CCN COc1ccc(cc1OC)c2[nH]c3ccccc3c2CCN 22 0 CCOC(=O)\C=N\CCc1c([nH]c2ccccc12)c3ccc(OC)c(OC)c3 V.Woodward VII.Woodward C1CCC(CC1)C2CC3CCCCC3N2 C1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 146-8 15 0 VII XI 118 64.4 1954 Woodward CCOC(=O)\C=N\CCc1c([nH]c2ccccc12)c3ccc(OC)c(OC)c3 CCOC(=O)\C=N\CCc1c([nH]c2ccccc12)c3ccc(OC)c(OC)c3 28 0 CCOC(=O)C1N(CCC12C(=Nc3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 VII.Woodward XI.Woodward C1CCC(CC1)C2CC3CCCCC3N2 C1CCC(CC1)C2NC3CCCCC3C24CCNC4 WoodwardC1CCC(CC1)C2CC3CCCCC3N2 WoodwardC1CCC(CC1)C2NC3CCCCC3C24CCNC4 170-80 19 0 XI XIV 11.2 85 1954 Woodward CCOC(=O)C1N(CCC12C(=Nc3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 CCOC(=O)C1N(CCC12C(=Nc3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 38 0 CCOC(=O)C1N(CC[C@]12[C@@H](Nc3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 XI.Woodward XIV.Woodward C1CCC(CC1)C2NC3CCCCC3C24CCNC4 C1CCC2C(C1)NCC23CCNC3 WoodwardC1CCC(CC1)C2NC3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)NCC23CCNC3 145-146 no 13 0 XIV XV 21.6 98.5 1954 Woodward CCOC(=O)C1N(CC[C@]12[C@@H](Nc3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 CCOC(=O)C1N(CC[C@]12[C@@H](Nc3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 38 0 CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 XIV.Woodward XV.Woodward C1CCC2C(C1)NCC23CCNC3 C1CCC2C(C1)NCC23CCNC3 WoodwardC1CCC2C(C1)NCC23CCNC3 WoodwardC1CCC2C(C1)NCC23CCNC3 180-1 no 13 0 XV XVI 2 29 1954 Woodward CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 41 0 CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)\C(=C\C(=O)OC)\C=C/C(=O)OC)S(=O)(=O)c4ccc(C)cc4 XV.Woodward XVI.Woodward C1CCC2C(C1)NCC23CCNC3 C1CCC2C(C1)NCC23CCNC3 WoodwardC1CCC2C(C1)NCC23CCNC3 WoodwardC1CCC2C(C1)NCC23CCNC3 206 no 13 0 XVI XX 1.31 75 1954 Woodward CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)\C(=C\C(=O)OC)\C=C/C(=O)OC)S(=O)(=O)c4ccc(C)cc4 CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)\C(=C\C(=O)OC)\C=C/C(=O)OC)S(=O)(=O)c4ccc(C)cc4 43 0 CCOC(=O)C1N(CC[C@]12C3=C(CC(=O)OC)C=CC(=O)N3c4ccccc24)S(=O)(=O)c5ccc(C)cc5 XVI.Woodward XX.Woodward C1CCC2C(C1)NCC23CCNC3 C1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)NCC23CCNC3 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 "two polymorphs, 165 and 184" no 13 0 XV XX 32 30 1954 Woodward CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 CCOC(=O)C1N(CC[C@]12[C@@H](N(C(=O)C)c3ccccc23)c4ccc(OC)c(OC)c4)S(=O)(=O)c5ccc(C)cc5 41 0 CCOC(=O)C1N(CC[C@]12C3=C(CC(=O)OC)C=CC(=O)N3c4ccccc24)S(=O)(=O)c5ccc(C)cc5 XV.Woodward XX.Woodward C1CCC2C(C1)NCC23CCNC3 C1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)NCC23CCNC3 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 206 no 17 0 XX XXVIII 1.4 72 1954 Woodward CCOC(=O)C1N(CC[C@]12C3=C(CC(=O)OC)C=CC(=O)N3c4ccccc24)S(=O)(=O)c5ccc(C)cc5 CCOC(=O)C1N(CC[C@]12C3=C(CC(=O)OC)C=CC(=O)N3c4ccccc24)S(=O)(=O)c5ccc(C)cc5 38 0 OC(=O)CC1=C2N(C(=O)C=C1)c3ccccc3[C@@]24CCNC4C(=O)O XX.Woodward XXVIII.Woodward C1CCC2C(C1)N3CCCCC3C24CCNC4 C1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 187-8 no 17 0 XXVIII Nacetylpyridonediacid 1.01 94.4 1954 Woodward OC(=O)CC1=C2N(C(=O)C=C1)c3ccccc3[C@@]24CCNC4C(=O)O OC(=O)CC1=C2N(C(=O)C=C1)c3ccccc3[C@@]24CCNC4C(=O)O 25 0 CC(=O)N1CC[C@@]2(C1C(=O)O)C3=C(CC(=O)O)C=CC(=O)N3c4ccccc24 XXVIII.Woodward Nacetylpyridonediacid.Woodward C1CCC2C(C1)N3CCCCC3C24CCNC4 C1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 ND no 17 0 Nacetylpyridonediacid XXIX 0.79 84 1954 Woodward CC(=O)N1CC[C@@]2(C1C(=O)O)C3=C(CC(=O)O)C=CC(=O)N3c4ccccc24 CC(=O)N1CC[C@@]2(C1C(=O)O)C3=C(CC(=O)O)C=CC(=O)N3c4ccccc24 28 0 COC(=O)CC1=C2N(C(=O)C=C1)c3ccccc3[C@@]24CCN(C4C(=O)OC)C(=O)C Nacetylpyridonediacid.Woodward XXIX.Woodward C1CCC2C(C1)N3CCCCC3C24CCNC4 C1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 275 no 17 0 XXIX XXX 2.2 87.5 1954 Woodward COC(=O)CC1=C2N(C(=O)C=C1)c3ccccc3[C@@]24CCN(C4C(=O)OC)C(=O)C COC(=O)CC1=C2N(C(=O)C=C1)c3ccccc3[C@@]24CCN(C4C(=O)OC)C(=O)C 30 0 COC(=O)C1=C(O)[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C XXIX.Woodward XXX.Woodward C1CCC2C(C1)N3CCCCC3C24CCNC4 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCCC3C24CCNC4 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 181-2 no 19 0 XXX XXXII 2.03 95 1954 Woodward COC(=O)C1=C(O)[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C COC(=O)C1=C(O)[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C 28 0 COC(=O)C1=C(OS(=O)(=O)c2ccc(C)cc2)[C@@H]3N(CC[C@]34C5=C1C=CC(=O)N5c6ccccc46)C(=O)C XXX.Woodward XXXII.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 200-205 no 19 0 XXXII XXXV 0.43 77 1954 Woodward COC(=O)C1=C(OS(=O)(=O)c2ccc(C)cc2)[C@@H]3N(CC[C@]34C5=C1C=CC(=O)N5c6ccccc46)C(=O)C COC(=O)C1=C(OS(=O)(=O)c2ccc(C)cc2)[C@@H]3N(CC[C@]34C5=C1C=CC(=O)N5c6ccccc46)C(=O)C 38 0 COC(=O)C1=C(SCc2ccccc2)[C@@H]3N(CC[C@]34C5=C1C=CC(=O)N5c6ccccc46)C(=O)C XXXII.Woodward XXXV.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 217 no 19 0 XXXV XXXVI 1.03 84 1954 Woodward COC(=O)C1=C(SCc2ccccc2)[C@@H]3N(CC[C@]34C5=C1C=CC(=O)N5c6ccccc46)C(=O)C COC(=O)C1=C(SCc2ccccc2)[C@@H]3N(CC[C@]34C5=C1C=CC(=O)N5c6ccccc46)C(=O)C 35 0 COC(=O)C1=C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C XXXV.Woodward XXXVI.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 256-7 no 19 0 XXXVI XXXVII 0.7 72.5 1954 Woodward COC(=O)C1=C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C COC(=O)C1=C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C 27 0 COC(=O)[C@@H]1C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C XXXVI.Woodward XXXVII.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 234 no 19 0 XXXVII XXXIX 1.21 59 1954 Woodward COC(=O)[C@@H]1C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C COC(=O)[C@@H]1C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C 27 0 CC(=O)N1CC[C@@]23[C@@H]1C[C@H](C(=O)O)C4=C2N(C(=O)C=C4)c5ccccc35 XXXVII.Woodward XXXIX.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 186 no 19 0 XXXIX XXXIX 0.71 21 1954 Woodward CC(=O)N1CC[C@@]23[C@@H]1C[C@H](C(=O)O)C4=C2N(C(=O)C=C4)c5ccccc35 CC(=O)N1CC[C@@]23[C@@H]1C[C@H](C(=O)O)C4=C2N(C(=O)C=C4)c5ccccc35 26 0 CC(=O)N1CC[C@@]23[C@@H]1C[C@H](C(=O)O)C4=C2N(C(=O)C=C4)c5ccccc35 XXXIX.Woodward XXXIX.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 284 no 19 0 XXXIX XL 0.57 27.5 1954 Woodward CC(=O)N1CC[C@@]23[C@@H]1C[C@H](C(=O)O)C4=C2N(C(=O)C=C4)c5ccccc35 CC(=O)N1CC[C@@]23[C@@H]1C[C@H](C(=O)O)C4=C2N(C(=O)C=C4)c5ccccc35 26 0 CC(=O)O\C(=C/1\C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C)\C XXXIX.Woodward XL.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 295-300 yes 19 0 XL XLIV 0.33 99 1954 Woodward CC(=O)O\C(=C/1\C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C)\C CC(=O)O\C(=C/1\C[C@@H]2N(CC[C@]23C4=C1C=CC(=O)N4c5ccccc35)C(=O)C)\C 29 0 CC(=O)[C@H]1C[C@@H]2NCC[C@]23C4=C1C=CC(=O)N4c5ccccc35 XL.Woodward XLIV.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 260-3 yes 19 0 XLIV XLV 0.33 12.4 1954 Woodward CC(=O)[C@H]1C[C@@H]2NCC[C@]23C4=C1C=CC(=O)N4c5ccccc35 CC(=O)[C@H]1C[C@@H]2NCC[C@]23C4=C1C=CC(=O)N4c5ccccc35 23 0 O=C1C=CC2=C3N1c4ccccc4[C@@]35CCN6[C@H]5C[C@H]2C(=O)C6=O XLIV.Woodward XLV.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 yes 21 13 XLV LXVI 0.63 53 1954 Woodward O=C1C=CC2=C3N1c4ccccc4[C@@]35CCN6[C@H]5C[C@H]2C(=O)C6=O O=C1C=CC2=C3N1c4ccccc4[C@@]35CCN6[C@H]5C[C@H]2C(=O)C6=O 24 13 O[C@@]1(C#C)[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O XLV.Woodward LXVI.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 172-4 yes 21 13 LXVI LXVII 1.45 86 1954 Woodward O[C@@]1(C#C)[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O O[C@@]1(C#C)[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O 26 13 O[C@@]1(C=C)[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O LXVI.Woodward LXVII.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 302-5 yes 21 13 LXVII LXVIII 0.75 30 1954 Woodward O[C@@]1(C=C)[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O O[C@@]1(C=C)[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O 26 13 O[C@@]1(CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46)C=C LXVII.Woodward LXVIII.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 244-5 yes 21 13 LXVIII LXIX 0.51 12.5 1954 Woodward O[C@@]1(CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46)C=C O[C@@]1(CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46)C=C 26 13 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 LXVIII.Woodward LXIX.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 192-200 yes 21 13 LXVIII isostrychnine acetates 0.51 33 1954 Woodward O[C@@]1(CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46)C=C O[C@@]1(CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46)C=C 26 13 CC(=O)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 LXVIII.Woodward isostrychnine acetates.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 192-200 yes 21 13 LXIX LXX 0.02 14 1954 Woodward OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 25 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 LXIX.Woodward LXX.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 208-12 yes 21 13 isostrychnine acetates LXX 0.17 14 1954 Woodward CC(=O)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 CC(=O)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 28 13 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 isostrychnine acetates.Woodward LXX.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 yes 24 25 LXX 299 24 1954 Woodward O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 O([C@H]1[C@]2([C@]3([C@]4(C5C[C@]2(C(=O)C(=O)N5CC4)[H])c2ccccc2N3C(=O)C1)[H])[H])CC(=O)O LXX.Woodward strychninonic acid.Woodward C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 WoodwardC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 278-85 yes 24 25 LXX strychninonic acid 299 24 1954 Woodward O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1c7ccccc67 25 25 O([C@H]1[C@]2([C@]3([C@]4(C5C[C@]2(C(=O)C(=O)N5CC4)[H])c2ccccc2N3C(=O)C1)[H])[H])CC(=O)O LXX.Woodward strychninonic acid.Woodward C1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCC4OCCC5CN6CCC27C6CC5C4C37 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 278-85 yes 21 13 strychninonic acid LVIII R=H 111 89 1954 Woodward O([C@H]1[C@]2([C@]3([C@]4(C5C[C@]2(C(=O)C(=O)N5CC4)[H])c2ccccc2N3C(=O)C1)[H])[H])CC(=O)O O([C@H]1[C@]2([C@]3([C@]4(C5C[C@]2(C(=O)C(=O)N5CC4)[H])c2ccccc2N3C(=O)C1)[H])[H])CC(=O)O 29 13 O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@@H]5[C@@H]2C=CC(=O)N5c6ccccc46)C1=O strychninonic acid.Woodward LVIII R=H.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 257-9 yes 21 13 LVIII R=H LVIII R=Ac 62.1 88 1954 Woodward O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@@H]5[C@@H]2C=CC(=O)N5c6ccccc46)C1=O O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@@H]5[C@@H]2C=CC(=O)N5c6ccccc46)C1=O 27 13 CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@@H]5[C@@H]2C=CC(=O)N5c6ccccc46)C1=O LVIII R=H.Woodward LVIII R=Ac.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 228-31 yes 21 13 LVIII R=Ac strychninolone b acetate LV 54.2 85 1954 Woodward CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@@H]5[C@@H]2C=CC(=O)N5c6ccccc46)C1=O CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@@H]5[C@@H]2C=CC(=O)N5c6ccccc46)C1=O 27 13 CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@H]5N(C(=O)CC=C25)c6ccccc46)C1=O LVIII R=Ac.Woodward strychninolone b acetate LV.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 242-4 yes 21 13 strychninolone b acetate LV dehydrostrychninolone acetate 25.5 86 1954 Woodward CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@H]5N(C(=O)CC=C25)c6ccccc46)C1=O CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34[C@H]5N(C(=O)CC=C25)c6ccccc46)C1=O 27 13 CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O strychninolone b acetate LV.Woodward dehydrostrychninolone acetate.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 135 yes 21 13 dehydrostrychninolone acetate Dehydrostrychninolone 19.3 92 1954 Woodward CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O CC(=O)O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O 24 13 O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O dehydrostrychninolone acetate.Woodward Dehydrostrychninolone.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 282-5 yes 21 13 Dehydrostrychninolone XLV 18.8 68 1954 Woodward O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O O[C@H]1[C@@H]2C[C@@H]3N(CC[C@]34C5=C2C=CC(=O)N5c6ccccc46)C1=O 24 13 O=C1C=CC2=C3N1c4ccccc4[C@@]35CCN6[C@H]5C[C@H]2C(=O)C6=O Dehydrostrychninolone.Woodward XLV.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 228-30 yes 21 13 XLV XXXVIII-acid 0.79 47.5 1954 Woodward O=C1C=CC2=C3N1c4ccccc4[C@@]35CCN6[C@H]5C[C@H]2C(=O)C6=O O=C1C=CC2=C3N1c4ccccc4[C@@]35CCN6[C@H]5C[C@H]2C(=O)C6=O 23 0 OC(=O)[C@H]1C[C@@H]2NCC[C@]23C4=C1C=CC(=O)N4c5ccccc35 XLV.Woodward XXXVIII-acid.Woodward C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 175-80 yes 19 0 XXXVIII-acid XXXIX 0.65 52 1954 Woodward OC(=O)[C@H]1C[C@@H]2NCC[C@]23C4=C1C=CC(=O)N4c5ccccc35 OC(=O)[C@H]1C[C@@H]2NCC[C@]23C4=C1C=CC(=O)N4c5ccccc35 26 0 CC(=O)N1CC[C@@]23[C@@H]1C[C@H](C(=O)O)C4=C2N(C(=O)C=C4)c5ccccc35 XXXVIII-acid.Woodward XXXIX.Woodward C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 WoodwardC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 305-8 yes 9 0 3-(indolyl)acetinitrile 3 15 82 2010 Reissig N#CCc1c[nH]c2ccccc12 N#CCc1c[nH]c2ccccc12 12 0 CCOC(=O)CCC(=O)CCC(=O)n1cc(CC#N)c2ccccc12 3-(indolyl)acetinitrile.Reissig 3.Reissig C1CCC2NCCC2C1 C1CCC2NCCC2C1 ReissigC1CCC2NCCC2C1 ReissigC1CCC2NCCC2C1 9 0 3 2 2 77 2010 Reissig CCOC(=O)CCC(=O)CCC(=O)n1cc(CC#N)c2ccccc12 CCOC(=O)CCC(=O)CCC(=O)n1cc(CC#N)c2ccccc12 25 0 O[C@@]12CCC(=O)N3[C@@H]1[C@@](CC#N)(C(=O)CC2)c4ccccc34 3.Reissig 2.Reissig C1CCC2NCCC2C1 C1CCC2C(C1)C3CCCC4CCCN2C34 ReissigC1CCC2NCCC2C1 ReissigC1CCC2C(C1)C3CCCC4CCCN2C34 95-98 16 0 2 22 1.62 97 2010 Reissig O[C@@]12CCC(=O)N3[C@@H]1[C@@](CC#N)(C(=O)CC2)c4ccccc34 O[C@@]12CCC(=O)N3[C@@H]1[C@@](CC#N)(C(=O)CC2)c4ccccc34 22 0 O[C@]12CC[C@@H]3NCC[C@]34[C@H]1N(C(=O)CC2)c5ccccc45 2.Reissig 22.Reissig C1CCC2C(C1)C3CCCC4CCCN2C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)C3CCCC4CCCN2C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 79-81 no 19 0 22 26 1.06 44 2010 Reissig O[C@]12CC[C@@H]3NCC[C@]34[C@H]1N(C(=O)CC2)c5ccccc45 O[C@]12CC[C@@H]3NCC[C@]34[C@H]1N(C(=O)CC2)c5ccccc45 21 0 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 22.Reissig 26.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 93-5 no 19 0 22 24 87 2010 Reissig O[C@]12CC[C@@H]3NCC[C@]34[C@H]1N(C(=O)CC2)c5ccccc45 O[C@]12CC[C@@H]3NCC[C@]34[C@H]1N(C(=O)CC2)c5ccccc45 21 0 COC(=O)N1CC[C@@]23[C@@H]1CC[C@]4(O)CCC(=O)N([C@H]24)c5ccccc35 22.Reissig 24.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 93-5 no 19 0 24 24-Ms 2010 Reissig COC(=O)N1CC[C@@]23[C@@H]1CC[C@]4(O)CCC(=O)N([C@H]24)c5ccccc35 COC(=O)N1CC[C@@]23[C@@H]1CC[C@]4(O)CCC(=O)N([C@H]24)c5ccccc35 25 0 COC(=O)N1CC[C@@]23[C@@H]1CC[C@@]4(CCC(=O)N([C@H]24)c5ccccc35)OS(=O)(=O)C 24.Reissig 24-Ms.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 >230 no 19 0 24-Ms 26 2010 Reissig COC(=O)N1CC[C@@]23[C@@H]1CC[C@@]4(CCC(=O)N([C@H]24)c5ccccc35)OS(=O)(=O)C COC(=O)N1CC[C@@]23[C@@H]1CC[C@@]4(CCC(=O)N([C@H]24)c5ccccc35)OS(=O)(=O)C 29 0 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 24-Ms.Reissig 26.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 26 32 0.43 65 2010 Reissig COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 24 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 26.Reissig 32.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 26 26.1 2010 Reissig COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 COC(=O)N1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 24 0 O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 26.Reissig 26.1.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 26.1 32 2010 Reissig O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 O=C1CCC2=CC[C@@H]3NCC[C@]34[C@H]2N1c5ccccc45 20 0 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 26.1.Reissig 32.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 no 19 0 32 33 0.095 68 2010 Reissig CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 33 0 CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 32.Reissig 33.Reissig C1CCC2C(C1)N3CCCC4CCC5NCCC25C34 C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 ReissigC1CCC2C(C1)N3CCCC4CCC5NCCC25C34 ReissigC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 no 21 13 33 2010 Reissig CC(C)(C)[Si](C)(C)OC\C=C/1\CN2CC[C@@]34[C@@H]2C[C@@H]1C5=CCC(=O)N([C@H]35)c6ccccc46 CC(C)(C)[Si](C)(C)OC\C=C(/I)\CN1CC[C@@]23[C@@H]1CC=C4CCC(=O)N([C@H]24)c5ccccc35 32 13 33.Reissig C1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 ReissigC1CCC2C(C1)N3CCCC4C5CCN6CCC2(C6C5)C34 . no