Synthetic Studies toward Phorboxazole A. Stereoselective Synthesis of the C₂₈−C₄₆ Side Chain Fragment

Abstract

A stereoselective synthesis of the C(28)-C(46) fragment (3) of phorboxazole A is described. Key advances include an enantioselective allylation to establish the stereochemistry of the tetrahydropyran unit and a useful SmI(2)-mediated modification of the Barbier reaction of iodomethyloxazole 15 with aldehyde 14.