The Asymmetric Total Synthesis of Cinbotolide: A Revision of the Original Structure
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- 作者：Jos茅 Manuel Botubol ; Mar铆a Jes煤s Dur谩n-Pe帽a ; Antonio J. Mac铆as-S谩nchez ; James R. Hanson ; Isidro G. Collado ; Rosario Hern谩ndez-Gal谩n
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：December 5, 2014
- 年：2014
- 卷：79
- 期：23
- 页码：11349-11358
- 全文大小：437K
- ISSN：1520-6904
文摘
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 纬-butyrolactone structure for the metabolite. This structure has been confirmed by an asymmetric total synthesis, which also established its absolute configuration.