A short diastereoselective synthesis of 1-aminoindolo-[2,3-a]quinolizidines via an N-acyliminium ion cyclisation

被引:21
作者
Ducrot, P [1 ]
Thal, C [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0040-4039(99)01922-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
trans 1-Aminoindolo[2,3-a]quinolizidines were synthesised using an intramolecular Pictet-Spengler-like reaction. Starting from commercially available N-Cbz-L-glutamic acid, indoloquinolizidines were obtained in only five steps with good yields. This improved synthesis is the result of both a highly regioselective imide reduction and a highly diastereoselective reaction using N-acyliminium ions. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9037 / 9040
页数:4
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