A METHOD FOR THE SYNTHESIS OF ALKYNYL PHENYL SULFIDES FROM ALKYNYLTRIMETHYLSILANES - A NOVEL, EFFICIENT SYNTHESIS OF THE THIENAMYCIN INTERMEDIATE FROM 3(R)-HYDROXYBUTYRIC ACID

被引:32
作者
MIYACHI, N [1 ]
SHIBASAKI, M [1 ]
机构
[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1021/jo00294a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The mechanism of the one-pot conversion of /3-amino thiol esters of type 3 to /3-lactams of type 4 has been clarified, and it is proposed that the actual active species is a PhSSPh-CuOTf complex. Through the use of this novel reaction, an efficient synthesis of the thienamycin intermediate 2, starting with 3(i?)-hydroxybutyric acid, has been achieved. Furthermore, the combined reagents (PhSSPh-CuOTf) have been demonstrated to be a powerful source of PhS+ through the conversion of several alkynyltrimethylsilanes to alkynyl phenyl sulfides. © 1990, American Chemical Society. All rights reserved.
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页码:1975 / 1976
页数:2
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