A unified strategy for the synthesis of the C1-C14 fragment of marinolic acids, mupirocins, pseudomonic acids and thiomarinols: total synthesis of pseudomonic acid methyl monate C.

A flexible stereoselective approach to the common C1-C14 skeleton present in natural products of the pseudomonic acid family is described. The strategy has been extended and the total synthesis of pseudomonic acid methyl monate C was achieved. The key synthetic reactions utilized include Achmatowicz rearrangement, Johnson-Claisen rearrangement, Julia-Kocienski olefination, and Horner-Wadsworth-Emmons olefination reaction.