合成方法wortmannilactone C。

Synthetic approach to wortmannilactone C.

机构信息

Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231, ESPCI ParisTech/CNRS/PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.

出版信息

Org Lett. 2015 Feb 20;17(4):816-9. doi: 10.1021/ol5036112. Epub 2015 Jan 29.

DOI:10.1021/ol5036112

PMID:25634559

Abstract

A diastereomer of wortmannilactone C has been synthesized according to a convergent and versatile strategy from tert-butyl 3-hydroxypropanoate and ethyl (R)-3-hydroxybutanoate. The key steps are a Liebeskind cross-coupling and a Horner-Wadsworth-Emmons (HWE) reaction to construct the macrolactone. The stereogenic centers at C9, C11, and C21 were controlled by enantioselective allyltitanations, and the C19 stereocenter was controlled by using a Noyori reduction of an acetylenic ketone.

摘要

根据从叔丁基 3-羟基丙酸酯和(R)-3-羟基丁酸乙酯出发的会聚和通用策略，已合成了wortmannilactone C 的非对映异构体。关键步骤是 Liebeskind 交叉偶联和 Horner-Wadsworth-Emmons（HWE）反应来构建大环内酯。C9、C11 和 C21 处的立体中心通过对映选择性烯丙基钛化来控制，而 C19 立体中心则通过乙酰基酮的 Noyori 还原来控制。