海葵内酯A的C(1)-C(11)片段的立体选择性合成。

Stereoselective synthesis of the C(1)-C(11) fragment of peloruside A.

作者信息

Owen Robert M, Roush William R

机构信息

Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.

出版信息

Org Lett. 2005 Sep 1;7(18):3941-4. doi: 10.1021/ol0514303.

DOI:10.1021/ol0514303

PMID:16119937

Abstract

A highly stereoselective synthesis of the C(1)-C(11) fragment 4 of peloruside A has been accomplished via a stereoselective double allylboration and an intramolecular epoxide opening to provide the functionally dense C(3)-C(11) segment 14. A glycolate aldol reaction was then employed to introduce the remaining stereocenters at C(2)-C(3). [reaction: see text]

摘要

通过立体选择性双烯丙基硼化反应和分子内环氧化合物开环反应，实现了对peloruside A的C(1)-C(11)片段4的高度立体选择性合成，从而得到功能密集的C(3)-C(11)片段14。然后采用乙醇酸醛醇反应在C(2)-C(3)处引入其余的立体中心。[反应：见正文]