ENANTIOSELECTIVE SYNTHESIS OF (+)-KJELLMANIANONE

被引：46

作者：

CHEN, BC

WEISMILLER, MC

DAVIS, FA

BOSCHELLI, D

EMPFIELD, JR

SMITH, AB

机构：

[1] DREXEL UNIV,DEPT CHEM,PHILADELPHIA,PA 19104

[2] UNIV PENN,RES STRUCT MATTER,DEPT CHEM,PHILADELPHIA,PA 19104

[3] UNIV PENN,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104

来源：

TETRAHEDRON | 1991年 / 47卷 / 02期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4020(01)80914-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)-kjellmanianone (1) has been achieved. The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of beta-keto ester 2 with the new, enantiomerically pure N-sulfonyloxaziridine 7b, affording 1 in 68.5% ee (60% yield). Possible transition state structures for the asymmetric oxidation are evaluated.

引用

收藏

页码：173 / 182

页数：10

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