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

页码：8941 / 8945

页数：5

共 28 条

[1] REACTIONS WITH INDOLE-DERIVATIVES .17. BIOGENETICALLY ORIENTATED TOTAL-SYNTHESIS OF DL-CAMPTOTHECIN AND 7-CHLOROCAMPTOTHECIN [J].