ELECTROCHEMICAL OXIDATION OF PROLINE DERIVATIVES - TOTAL SYNTHESES OF BULGECININE AND BULGECIN-C

被引：84

作者：

BARRETT, AGM ^{[1
]}

PILIPAUSKAS, D ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 08期

关键词：

D O I：

10.1021/jo00008a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.

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页码：2787 / 2800

页数：14

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