（-）-红藻氨酸的立体控制全合成。用（+）-鹰爪豆碱类似物对吡咯烷环进行区域和立体选择性锂化反应。

Stereocontrolled total synthesis of (-)-kainic acid. Regio- and stereoselective lithiation of pyrrolidine ring with the (+)-sparteine surrogate.

作者信息

Morita Yasuhiro, Tokuyama Hidetoshi, Fukuyama Tohru

机构信息

Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo 113-0033, Japan.

出版信息

Org Lett. 2005 Sep 29;7(20):4337-40. doi: 10.1021/ol051408+.

DOI:10.1021/ol051408+

PMID:16178527

Abstract

[reaction: see text] A stereocontrolled total synthesis of (-)-kainic acid is described. cis-3,4-Disubstituted pyrrolidine ring was constructed by [3 + 2] cycloaddition of azomethine ylide with chiral butenolide. The crucial introduction of carboxyl group at the C-2 position was executed by regio- and stereoselective lithiation of the pyrrolidine ring in the presence of a (+)-sparteine surrogate followed by trapping with carbon dioxide.

摘要

[反应：见正文] 描述了（-）-海藻酸的立体控制全合成。通过甲亚胺叶立德与手性丁烯内酯的[3 + 2]环加成反应构建了顺式-3,4-二取代吡咯烷环。在（+）-鹰爪豆碱替代物存在下，通过吡咯烷环的区域和立体选择性锂化反应，随后用二氧化碳捕获，实现了在C-2位关键引入羧基。