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

José Manuel BotubolAres | Zendy; María Jesús DuránPeña | Zendy; Antonio J. MacíasSánchez | Zendy; James R. Hanson | Zendy; Isidro G. Collado | Zendy; Rosario HernándezGalán | Zendy

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

Author(s) -

José Manuel BotubolAres,

María Jesús DuránPeña,

Antonio J. MacíasSánchez,

James R. Hanson,

Isidro G. Collado,

Rosario HernándezGalán

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo501471m

Subject(s) - botrytis cinerea , metabolite , stereochemistry , mutant , absolute configuration , total synthesis , chemical structure , secondary metabolite , chemistry , biology , botany , biochemistry , organic chemistry , gene

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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