A highly stereoselective and practical total synthesis of the tricyclic beta-lactam antibiotic GV104326 (4-methoxytrinem)

被引：42

作者：

Hanessian, S

Rozema, MJ

机构：

[1] Department of Chemistry, Université de Montréal, Montréal, Que. H3C 3J7, P. O. Box 6128, Succ. Centre-Ville

[2] Abbott Laboratories, Abbott Park, North Chicago

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 41期

关键词：

D O I：

10.1021/ja962006n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and practical total synthesis of a tricyclic beta-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.

引用

页码：9884 / 9891

页数：8