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

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

Authors :
Botubol JM
Durán-Peña MJ
Macías-Sánchez AJ
Hanson JR
Collado IG
Hernández-Galán R
Source :
The Journal of organic chemistry [J Org Chem] 2014 Dec 05; Vol. 79 (23), pp. 11349-58. Date of Electronic Publication: 2014 Nov 14.
Publication Year :
2014

Abstract

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.

Details

Language :
English
ISSN :
1520-6904
Volume :
79
Issue :
23
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
25372296
Full Text :
https://doi.org/10.1021/jo501471m