环间 O-杂环化：一种用于 Murisolin 和 16,19-顺式-Murisolin 全合成的有用工具。

Transannular O-heterocyclization: a useful tool for the total synthesis of Murisolin and 16,19-cis-Murisolin.

机构信息

Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, D-48149 Münster, Germany.

出版信息

Org Lett. 2012 Nov 16;14(22):5628-31. doi: 10.1021/ol302820c. Epub 2012 Nov 8.

Abstract

Transannular O-heterocyclization is applied as a key step in a total synthesis. This highly stereoselective and metal-free transformation introduces four stereocenters in one step. It was chosen to be the pivotal step in the synthesis of Murisolin and 16,19-cis-Murisolin, two annonaceous acetogenins. The efficiency of this synthesis is further illustrated by a stereodivergent late-stage separation of both synthetic routes.

摘要

环间 O-杂环化被应用于全合成的关键步骤中。这是一个高度对映选择性且无需金属的转化，可在一步中引入四个手性中心。它被选为合成 Murisolin 和 16,19-顺式-Murisolin 这两种番荔枝内酯的关键步骤。这种合成方法的效率还通过两种合成途径的后期立体发散性分离得到了进一步证明。