jo9b02918_si_003.cif (1001.81 kB)

Total Syntheses of (−)-Deoxoapodine, (−)-Kopsifoline D, and (−)-Beninine

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posted on 26.12.2019, 20:43 by Yi-Guo Zhou, Henry N. C. Wong, Xiao-Shui Peng
The total syntheses of Aspidosperma and Kopsia alkaloids (−)-deoxoapodine, (−)-kopsifoline D, and (−)-beninine are described through a domino deprotection-Michael addition-nucleophilic substitution protocol to assemble the core framework in efficient steps. Corey–Bakshi–Shibata reduction was employed to afford the enantioenriched intermediate for the total syntheses of the aforementioned alkaloids. The chirality was shown to completely transfer to the backbone using Johnson–Claisen rearrangement. The enantioselective total syntheses of (−)-kopsifoline D and (−)-beninine were accomplished for the first time. Our strategy opens up practical avenues for the total synthesis of structurally similar alkaloids.