SYNTHESIS OF (2RS,E)-3-ETHYLIDENE-AZETIDINE-2-CARBOXYLIC ACID (RAC POLYOXIMIC ACID)

被引：38

作者：

EMMER, G

机构：

[1] Sandoz Forschungsinstitut, A-1230 Wien

来源：

TETRAHEDRON | 1992年 / 48卷 / 35期

关键词：

(2RS; E)-3-ETHYLIDENE-2-CARBOXYLIC ACID; (+-) POLYOXIMIC ACID; POLYOXINS;

D O I：

10.1016/S0040-4020(01)88257-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of alpha-diazo beta-ketoester 4 with a catalytic amount of rhodium (II) acetate followed by Wittig reaction with phosphorane 5 gave the isomeric phenylthioester derivative 6a and 6b. Reduction of 6a led to the corresponding allylic alcohol 7, which was further converted into the bromide 8. Dehalogenation of 8 with NaBH4/DMF resulted in compound 9, which was deprotected with trifluoroacetic acid, giving racemic polyoximic acid (1).

引用

收藏

页码：7165 / 7172

页数：8

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