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羟基吡咯烷的简洁和立体选择性合成:(+)-普雷辛的快速合成。

A concise and stereoselective synthesis of hydroxypyrrolidines: rapid synthesis of (+)-preussin.

机构信息

Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada.

出版信息

Org Lett. 2010 Sep 17;12(18):4034-7. doi: 10.1021/ol101631e.

DOI:10.1021/ol101631e
PMID:20726562
Abstract

A convergent and stereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidines has been developed that involves reductive annulation of β-iminochlorohydrins, which are readily available from β-ketochlorohydrins, and provides rapid access to a variety of 2,5-syn-pyrrolidines. Application of this process to the concise (three-step) synthesis of the fungal metabolite (+)-preussin and analogues of this substance is reported.

摘要

已开发出一种 2,5-二取代 3-羟基吡咯烷的收敛和立体选择性合成方法,该方法涉及β-亚氨基氯醇的还原环化,β-酮氯醇很容易得到,并且可以快速获得各种 2,5-顺式吡咯烷。该方法已应用于真菌代谢产物(+)-普雷辛及其类似物的简洁(三步)合成。

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