A Concise Synthesis of Bengamide E and Analogues via E-Selective Cross-Metathesis Olefination

被引：7

作者：

Alam, Safiul ^{[1
]}

Dhimane, Hamid ^{[1
]}

机构：

[1] Univ Paris 05, CNRS, Chim & Biochim Pharmacol & Toxicol Lab, UFR Biomed,UMR 8601, F-75270 Paris 06, France

来源：

SYNLETT | 2010年 / 19期

关键词：

bengamide; analogues; cross-metathesis; stereoselective olefination; isomerization; RUTHENIUM CARBENE; AMINO-ACIDS; METHIONINE; ISOMERIZATION; STEREOCHEMISTRY; CAPROLACTAM; PROTEOMICS; MILD;

D O I：

10.1055/s-0030-1259015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modular, eight-step synthesis of bengamide E and six analogues from a common chiral pool has been developed. The key step in this approach is a cross-metathesis coupling of various commercial terminal olefins and a common alkene bearing the required stereogenic centers of bengamides lateral chain, which was easily derived from alpha-D-glucoheptonic-gamma-lactone. Complete E-selectivity, and up to 92% yield were achieved for this crucial cross-metathesis step.

引用

页码：2923 / 2927

页数：5

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