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Concise and efficient synthesis of calothrixin B.

Drissa Sissouma·Lucie Maingot·Sylvain Collet·André Guingant
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Abstract

A convergent synthesis of the naturally occurring alkaloid Calothrixin B is presented, which used a regioselective hetero-Diels-Alder reaction between a "push-pull" 2-aza-diene and a N-protected 3-bromo-9H-carbazole-1,4-dione to construct the five-ring skeleton of the molecule. Protection of the indole motif with a benzyl group was unattractive for delivery of sufficient target material because the removal of the protecting group had not been high yielding. We therefore elected to temporarily protect the indole motif with a more labile benzyloxycarbonyl group. Accordingly, the synthesis of calothrixin B proceeded in 17% overall yield over 9 steps from the commercially available 1,2,3,9-tetrahydro-4H-carbazol-4-one.

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AntimalarialsAntineoplastic AgentsCarbazolesCyclizationIndole AlkaloidsMolecular StructureOxidation-ReductionEvaluation StudyJournal ArticleResearch Support, Non-U.S. Gov't

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Drissa Sissouma, Lucie Maingot, Sylvain Collet, André Guingant. 2006-10-27. Concise and efficient synthesis of calothrixin B.. https://doi.org/10.1021/jo061270o

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