一种合成手性多羟基中氮茚和喹嗪的短路线。

A short route toward chiral, polyhydroxylated indolizidines and quinolizidines.

作者信息

Verhelst Steven H L, Paez Martinez Baltasar, Timmer Mattie S M, Lodder Gerrit, van der Marel Gijsbert A, Overkleeft Herman S, van Boom Jacques H

机构信息

Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.

出版信息

J Org Chem. 2003 Dec 12;68(25):9598-603. doi: 10.1021/jo0350662.

DOI:10.1021/jo0350662

PMID:14656083

Abstract

In this paper, a rapid route toward functionalized bicyclic alkaloids is presented. In only three steps, an easily accessible carbohydrate derivative was converted into iodomethyl indolizidine 13, which can equilibrate to the corresponding iodoquinolizidine 15. We provide strong evidence that this equilibration proceeds via an aziridinium ion intermediate. Furthermore, nucleophilic substitution of the iodomethyl indolizidine as well as the aziridinium intermediate gives access to highly functionalized indolizidine and quinolizidine alkaloids.

摘要

本文介绍了一种通往功能化双环生物碱的快速途径。只需三步，一种易于获得的碳水化合物衍生物就被转化为碘甲基中氮茚13，它可以与相应的碘喹嗪15达到平衡。我们提供了有力证据表明这种平衡是通过氮杂环丙烷离子中间体进行的。此外，碘甲基中氮茚以及氮杂环丙烷中间体的亲核取代反应可得到高度功能化的中氮茚和喹嗪生物碱。