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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.
- 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