通过非对映体选择性RCM反应合成（+）-peloruside A的C12-C19片段。

Synthesis of the C12-C19 fragment of (+)-peloruside A through a diastereomer-discriminating RCM reaction.

作者信息

Roulland Emmanuel, Ermolenko Mikhail S

机构信息

Institut de Chimie des Substances Naturelles, CNRS, avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

出版信息

Org Lett. 2005 May 26;7(11):2225-8. doi: 10.1021/ol050588k.

DOI:10.1021/ol050588k

PMID:15901175

Abstract

[reaction: see text]. A short and efficient asymmetric synthesis of the C12-C19 fragment of the cytotoxic macrolide (+)-peloruside A has been achieved via a highly diastereomer-discriminating RCM of alpha-branched but-3-enoate ester of a methallylic alcohol derived from hydrolytically resolved (S)-(-)-propylene oxide.

摘要

[反应：见正文]。通过对水解拆分得到的(S)-(-)-环氧丙烷衍生的甲基烯丙醇的α-支链-3-烯酸酯进行高度非对映体选择性的RCM反应，实现了细胞毒性大环内酯(+)-peloruside A的C12-C19片段的短程高效不对称合成。