The Asymmetric Total Synthesis of Cinbotolide: A Revision of the Original Structure

Abstract

The structure 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (<b>1</b>) was assigned to a metabolite of <i>Botrytis cinerea</i>, but the spectra of several synthetic analogues had significant differences from that of <b>1</b>. Examination of the constituents of a <i>B. cinerea</i> mutant that overproduces polyketides gave sufficient quantities of <b>1</b>, now named cinbotolide, for chemical transformations. These led to a revised γ-butyrolactone structure for the metabolite. This structure has been confirmed by an asymmetric total synthesis, which also established its absolute configuration