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.

引用

页码：11349 / 11358

页数：10

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