(+)-戈尼二醇的高度对映选择性全合成。

A highly enantioselective total synthesis of (+)-goniodiol.

作者信息

Tate Edward W, Dixon Darren J, Ley Steven V

机构信息

Biological and Biophysical Chemistry Section, Department of Chemistry, Imperial College London, UK.

出版信息

Org Biomol Chem. 2006 May 7;4(9):1698-706. doi: 10.1039/b602805e. Epub 2006 Mar 27.

DOI:10.1039/b602805e

PMID:16633562

Abstract

A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric centre, facilitating the rapid and diastereoselective construction of this functionalised system.

摘要

以易得的(S)-缩水甘油为起始原料，实现了具有生物活性的苯乙烯基内酯(+)-戈尼二醇的高产率对映选择性全合成。关键步骤是通过异头中心连接的硅烯醇醚的氧到碳重排，这有助于快速且非对映选择性地构建这个官能化体系。