Total synthesis of (+)-conagenin

被引：45

作者：

Hatakeyama, S

Fukuyama, H

Mukugi, Y

Irie, H

机构：

[1] Faculty of Pharmaceutical Sciences, Nagasaki University

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 23期

关键词：

D O I：

10.1016/0040-4039(96)00758-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved in highly stereo- and enantioselective manner. The carboxylic acid moiety was synthesized starting with asymmetric aldol reaction of propiophenone with acetaldehyde followed by in situ syn-selective NaBH4 reduction. The amino acid moiety was synthesized based upon Et(2)AlCl catalyzed cyclization of the epoxy trichloroacetimidate prepared from (S)-methylglycidol. Condensation of both moieties and alkaline hydrolysis led to (+)-conagenin. (C) 1996 Elsevier Science Ltd.

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页码：4047 / 4050

页数：4

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