A STEREOSELECTIVE SYNTHESIS OF THE DIHYDROXYETHYLENE DIPEPTIDE ISOSTERE, A-82768

被引：11

作者：

KRYSAN, DJ ^{[1
]}

HAIGHT, AR ^{[1
]}

MENZIA, JA ^{[1
]}

WELCH, N ^{[1
]}

机构：

[1] ABBOTT LABS,DIV PROC RES CHEM & AGR PROD,ABBOTT PK,IL 60064

来源：

TETRAHEDRON | 1994年 / 50卷 / 21期

关键词：

DIHYDROXYETHYLENE DIPEPTIDE ISOSTERE; DIASTEREOSELECTIVE GRIGNARD ADDITION TO AN ALPHA; BETA-EPOXY ALDEHYDE;

D O I：

10.1016/S0040-4020(01)80638-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereocontrolled synthesis of the dihydroxyethylene dipeptide isostere, A-82768, 1 via an erythro-selective addition of a Grignard reagent to a cis alpha,beta-epoxy aldehyde is described. The resulting erythro-epoxy alcohol was converted to the desired 3-amino-1,2-diol in a two step sequence which made use of a regioselective azide addition reaction. Procedures for the resolution of racemic 1 as well as the enantiomeric purification of scalemic 1 are also presented.

引用

页码：6163 / 6172

页数：10

共 29 条

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