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

被引：12
|
作者：
Manuel Botubol, Jose [1 ]
Jesus Duran-Pena, Maria [1 ]
Macias-Sanchez, Antonio J. [1 ]
Hanson, James R. [2 ]
Collado, Isidro G. [1 ]
Hernandez-Galan, Rosario [1 ]
机构：
[1] Univ Cadiz, Inst Biomol, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
[2] Univ Sussex, Dept Chem, Brighton BN1 9QJ, E Sussex, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 23期
关键词：
ABSOLUTE-CONFIGURATION; BOTRYTIS-CINEREA; ALLYLIC ALCOHOLS; LACTONES; BOTCINOLIDE; DERIVATIVES; ASSIGNMENT;
D O I：
10.1021/jo501471m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 gamma-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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收藏
页码：11349 / 11358
页数：10
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