Total synthesis of (-)-bitungolide F and determination of its absolute stereochemistry

被引：24

作者：

Ghosh, Subhash ^{[1
]}

Kumar, Soma Uday ^{[1
]}

Shashidhar, J. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 04期

关键词：

D O I：

10.1021/jo7023152

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly convergent total synthesis of bitungolide F leading to the assignment of its absolute stereochemistry is described. The key steps include a Horner-Wadsworth-Emmons olefination to construct the C7-C8 bond, a Wittig reaction to introduce the conjugate E,E-olefinic moiety in the molecule, and finally a ring-closing metathesis reaction to construct the six-membered alpha,beta-unsaturated delta-lactone of the molecule. Modified Evans's syn-aldol reaction, using Crimmins's protocol, was used to install the stereochemistries at the C4 and C5 centers. The stereochemistry at C9 was introduced by means of hydroxy-directed reduction of the C9 keto using Evans's protocol.

引用

页码：1582 / 1585

页数：4

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