Synthesis of the non-classical acetogenin mucocin: a modular approach based on olefinic coupling reactions

Abstract

A three component modular synthesis of the potent antitumor agent mucocin, based on olefinic coupling reactions, is described. A cross-metathesis on tetrahydropyran and tetrahydrofuran alkene components was used to assemble a stereochemically complex, non-adjacently-linked bicyclic ether. The latter was elaborated to a sulfone and partnered with a butenolide aldehyde component in a Julia–Kocienski olefination to provide the mucocin framework, which was converted to the natural product after hydrogenation and alcohol deprotection.