Rapid synthesis of the tetrahydroquinoline alkaloids: angustureine, cuspareine and galipinine

被引：56

作者：

O'Byrne, Aisling ^{[1
]}

Evans, Paul ^{[1
]}

机构：

[1] Natl Univ Ireland Univ Coll Dublin, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

TETRAHEDRON | 2008年 / 64卷 / 35期

关键词：

tetrahydroquinoline; organolithium; natural product; anti-malarial;

D O I：

10.1016/j.tet.2008.06.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot method for the preparation of 1,2-substituted dihydroquinolines is described. This method features the C-2 addition of a range of organolithium reagents to quinoline followed by the in-situ addition of an electrophile. Standard palladium-catalysed hydrogenation, of the resultant 1,2-disubstituted dihydroquinoline adducts, generates the corresponding 1,2-disubstituted tetrahydroquinoline. A series of such compounds have been synthesised including the natural products; (+/-)-angustureine 1, cuspareine 2 and galipinine 3. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：8067 / 8072

页数：6

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