具有三个连续手性中心的邻氨基二醇亚基的2-吡咯烷酮的互补立体控制方法：（-）-去毒素宁的形式不对称合成。

Complementary stereocontrolled approaches to 2-pyrrolidinones bearing a vicinal amino diol subunit with three continuous chiral centers: a formal asymmetric synthesis of (-)-detoxinine.

作者信息

Zhou Xiang, Liu Wen-Jun, Ye Jian-Liang, Huang Pei-Qiang

机构信息

Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, PR China.

出版信息

J Org Chem. 2007 Nov 9;72(23):8904-9. doi: 10.1021/jo7018784. Epub 2007 Oct 20.

DOI:10.1021/jo7018784

PMID:17949109

Abstract

We report herein two stereocomplementary approaches to erythro/trans and threo/cis vicinal amino diol subunits containing 2-pyrrolidinones (9 and 10) starting from the known enamides 7, easily available from malimides. The first approach consists of an epoxidation-reductive dehydroxylation procedure, and the second one is based on hydroboration-oxidation reactions. Using the second method, a formal asymmetric synthesis of (-)-detoxinine was achieved.

摘要

我们在此报告了两种立体互补方法，用于从已知的烯酰胺7开始合成含有2-吡咯烷酮（9和10）的赤式/反式和顺式/顺式邻位氨基二醇亚基，烯酰胺7可从马来酰亚胺轻松获得。第一种方法包括环氧化-还原脱羟基过程，第二种方法基于硼氢化-氧化反应。使用第二种方法，实现了（-）-去毒素宁的形式不对称合成。