立体等控制合成螺环橄榄烷，sequosempervirin A：绝对构型的修订。

Integral stereocontrolled synthesis of a spiro-norlignan, sequosempervirin A: revision of absolute configuration.

机构信息

Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.

出版信息

Org Lett. 2011 Sep 2;13(17):4640-3. doi: 10.1021/ol2018533. Epub 2011 Aug 1.

DOI:10.1021/ol2018533

Abstract

A novel synthetic path to sequosempervirin A was established by employing a samarium diiodide promoted intramolecular Barbier-type reaction of the lactonic iodide, in which the key structural feature, a spiro[4.5]decane ring system, could be constructed by controlling the stereochemistry of the hydroxyl group at the 8-position. The absolute configuration of natural sequosempervirin A was revised to be 4S based on this synthesis.

摘要

建立了一种新颖的合成序列霉素 A 的方法，通过 SmI2 促进内酯碘化的分子内 Barbier 型反应，其中关键的结构特征，螺[4.5]癸烷环系统，可以通过控制 8 位羟基的立体化学来构建。基于该合成，天然序列霉素 A 的绝对构型被修订为 4S。