An efficient and convenient approach to the total synthesis of sphingofungin

被引：47

作者：

Liu, DG ^{[1
]}

Wang, B ^{[1
]}

Lin, GQ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 26期

关键词：

D O I：

10.1021/jo005612g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As a new member of the sphingofungin family, sphingofungin F exhibits interesting physiological activities-with a structural unit of an a-substituted alanine. Described herein is an efficient and convenient stereoselective synthesis of sphingofungin F from L-(+)-tartaric acid, which utilizes Sharpless asymmetric epoxidation of allylic alcohol and Lewis acid-catalyzed intramolecular epoxide-opening reaction with an N-nucleophile, to introduce the other two desired stereogenic centers. Side chain functionality was incorporated into the chiral segment using a Wittig reaction.

引用

页码：9114 / 9119

页数：6

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