STUDIES ON THE TOTAL SYNTHESIS OF LACTACYSTIN - AN IMPROVED ALDOL COUPLING REACTION AND A BETA-LACTONE INTERMEDIATE IN THIOL ESTER FORMATION

被引：71

作者：

COREY, EJ

REICHARD, GA

KANIA, R

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(00)61575-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The recently developed total synthesis of lactacystin (1) has been improved by using the zirconium enolate derived from (R)- or (S)-2-siloxy-1,2,2-triphenylpropionate which lead stereospecifically to either (6S,7R) or (6R,7S) lactacystin, respectively. The formation of the thiol ester in the synthesis of 1 proceeds mainly via a beta-lactone intermediate.

引用

页码：6977 / 6980

页数：4

共 5 条

[1] ANTI-SELECTIVE AND DIASTEREOFACIALLY SELECTIVE ALDOL REACTIONS WITH (R)-2-SILOXY-1,2,2-TRIPHENYLETHYL PROPIONATE [J].