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
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.
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页码:9884 / 9891
页数:8
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