An 18-step synthesis of (−)-enigmazole A is herein disclosed. The present synthesis is based on a modular assembly of three building blocks of similar complexity, a macrocyclic ring-closing metathesis to forge the 18-membered macrocyclic skeleton, and a desilylative transannular oxa-Michael addition for stereoselective construction of the 2,6-cis-substituted tetrahydropyran ring.
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Masuda et al. (2024) studied this question.
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