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Enantioselective Formal Synthesis of (+)-Cycloclavine and Total Synthesis of (+)-5-epi-Cycloclavine

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journal contribution
posted on 14.08.2019, 13:39 by Wei Wang, Yang Mi, Xiao-Ping Cao, Zi-Fa Shi
Starting from the commercially available 4-bromoindole, a concise and efficient enantioselective formal synthesis of (+)-cycloclavine (1) in 13 steps with 2.0% overall yield and a total synthesis of (+)-5-epi-cycloclavine (2) in 14 steps with 3.3% overall yield were achieved. Key features of the syntheses include the addition of a Grignard reagent to the CN/Heck reaction sequence to construct the fused 6–5–6 ring systems, cyclopropanation, an ester aminolysis reaction, and the first example of the construction of a 3-azabicyclo­[3,1,0]­hexane through an intramolecular [3 + 2] cycloaddition/nitrogen extrusion.