The asymmetric total synthesis of cinbotolide: a revision of the original structure.

J Org Chem

Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biomoléculas, Campus Universitario Rio San Pedro s/n, Universidad de Cádiz , 11510 Puerto Real, Cádiz, Spain.

Published: December 2014

The structure 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1) was assigned to a metabolite of Botrytis cinerea, but the spectra of several synthetic analogues had significant differences from that of 1. Examination of the constituents of a B. cinerea mutant that overproduces polyketides gave sufficient quantities of 1, 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.

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http://dx.doi.org/10.1021/jo501471mDOI Listing

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