Abstract
Filipin III ( 1), a polyene macrolide antibiotic, has been synthesized for the first time. The polyol chain was assembled using a stereoselective carbon-carbon bond forming strategy previously developed in our lab: a cyanohydrin acetonide alkylation and reductive decyanation sequence. The polyene segment was prepared from L-ascorbic acid. These two components were coupled using Yamaguchi's esterification, and cyclized with an intramolecular Horner-Emmons reaction to form a trisubstituted alkene. Stereoselective reduction followed by deprotection gave filipin III. This highly convergent approach to filipin III represents the first total synthesis of a methylpentaene macrolide antibiotic.
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