D-赤藓糖型鞘氨醇、L-苏阿糖型鞘氨醇及其区域异构体的发散合成。

Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers.

作者信息

Olofsson Berit, Somfai Peter

机构信息

Department of Chemistry, Organic Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden.

出版信息

J Org Chem. 2003 Mar 21;68(6):2514-7. doi: 10.1021/jo0268254.

DOI:10.1021/jo0268254

PMID:12636430

Abstract

Starting from a vinyl epoxide, a divergent synthesis of four sphingosine isomers is described. The remaining four isomers can easily be synthesized using the same methodology. Although numerous syntheses of sphingosine have been published, this is the first general route leading to all eight isomers in this important compound class. The synthetic strategy relies on regioselective opening of a vinyl epoxide and a vinylaziridine in the allylic position.

摘要

从乙烯基环氧化合物出发，描述了一种对四种鞘氨醇异构体的发散性合成方法。使用相同的方法可以轻松合成其余四种异构体。尽管已经发表了许多关于鞘氨醇的合成方法，但这是首次能通向该重要化合物类别中所有八种异构体的通用路线。该合成策略依赖于烯丙基位置的乙烯基环氧化合物和乙烯基氮杂环丙烷的区域选择性开环反应。