Enantiospecific Total Synthesis of (−)-Bakkenolide III and Formal Total Synthesis of (−)-Bakkenolides B, C, H, L, V, and X

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Abstract

A concise enantiospecific synthesis of (-)-bakkenolide III was accomplished from (S)-(+)-carvone. The key step involved radical cyclization of an iodoketone intermediate which afforded the cis-hydrindanone skeleton. Further synthetic transformations generated bakkenolide III, which also constitutes the formal total synthesis of (-)-bakkenolides, B, C, H, L, V, and X.

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