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??

Organic & Biomolecular Chemistry Pub Date: 2014-02-27 DOI: 10.1039/C4OB00025K

Abstract

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.

Graphical abstract: 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
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