Synthesis of optically pure pyrroloquinolones via Pictet-Spengler and Winterfeldt reactions

被引：28
|
作者：
Jiang, WQ
Sui, ZH
Chen, X
机构：
[1] Johnson & Johnson Pharmaceut Res & Dev LLC, Drug Discovery, Raritan, NJ 08869 USA
[2] Johnson & Johnson Pharmaceut Res & Dev LLC, Comp Aided Drug Discovery, Raritan, NJ 08869 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 49期
关键词：
D O I：
10.1016/S0040-4039(02)02147-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diastereomers of substituted 2,3,4,9-tetrahydro-1H-beta-carbolines were synthesized via asymmetric Pictet-Spengler reaction of the chiral tryptamine derived from R-1-naphthalen-1-yl-ethylamine with 67% of d.e. The S,R-beta-carboline can be converted to the R,R form by treating with TFA. Optically pure pyrroloquinolones were obtained from Winterfeldt oxidation of the beta-carbolines without epimerization. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8941 / 8945
页数：5
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