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

被引：55
|
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
收藏
页码：8067 / 8072
页数：6
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