α-生育酚的非对映选择性合成：色满醇形成的新概念。

Diastereoselective synthesis of alpha-tocopherol: a new concept for the formation of chromanols.

作者信息

Chapelat Julien, Buss Axel, Chougnet Antoinette, Woggon Wolf-D

机构信息

Department of Chemistry, University of Basel, Basel, Switzerland.

出版信息

Org Lett. 2008 Nov 20;10(22):5123-6. doi: 10.1021/ol8019583. Epub 2008 Oct 21.

DOI:10.1021/ol8019583

PMID:18937482

Abstract

A diastereoselective synthesis of alpha-tocopherol 1 (93% de) was achieved via two key steps, (i) a highly diastereoselective Shi epoxidation of a trisubstituted alkene and (ii) an acid supported, "anti-Baldwin" epoxide ring opening under inversion of configuration leading to the 6-membered chromanol ring.

摘要

通过两个关键步骤实现了α-生育酚1的非对映选择性合成（非对映体过量93%），（i）三取代烯烃的高度非对映选择性施氏环氧化反应，以及（ii）在构型翻转下酸促进的“反鲍德温”环氧开环反应，生成六元色满醇环。