苯并[a]喹嗪和吲哚并[2,3-a]喹嗪对映选择性合成的直接方法。

Straightforward methodology for the enantioselective synthesis of benzo[a]- and indolo[2,3-a]quinolizidines.

作者信息

Amat Mercedes, Santos Maria M M, Bassas Oriol, Llor Núria, Escolano Carmen, Gómez-Esqué Arantxa, Molins Elies, Allin Steven M, McKee Vickie, Bosch Joan

机构信息

Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.

出版信息

J Org Chem. 2007 Jul 6;72(14):5193-201. doi: 10.1021/jo070539g. Epub 2007 Jun 5.

DOI:10.1021/jo070539g

PMID:17547461

Abstract

An enantioselective two-step route to substituted benzo[a]- and indolo[2,3-a]quinolizidines has been developed. It consists of (i) a stereoselective cyclocondensation of a racemic or prochiral delta-oxo(di)ester with either (S)-(3,4-dimethoxyphenyl)alaninol or (S)-tryptophanol in a process involving a dynamic kinetic resolution and/or the differentiation of enantiotopic or diastereotopic ester groups, and (ii) a subsequent stereocontrolled cyclization on the aromatic ring taking advantage of the masked N-acyl iminium ion present in the resulting oxazolopiperidone lactams.

摘要

已开发出一种对映选择性两步法合成取代苯并[a]-和吲哚[2,3-a]喹诺里西啶的路线。该路线包括：(i) 外消旋或前手性δ-氧代（二）酯与(S)-(3,4-二甲氧基苯基)丙氨醇或(S)-色醇进行立体选择性环缩合反应，此过程涉及动态动力学拆分和/或对映异位或非对映异位酯基的区分；(ii) 利用所得恶唑并哌啶酮内酰胺中存在的掩蔽N-酰基亚胺离子，随后在芳环上进行立体控制环化反应。