Tandem carbophilic addition-N-acyliminium ion cyclization for the synthesis of functionalized pyrrolo[2,1-a]isoquinolones: Key intermediates for the preparation of Erythrina-type alkaloids

被引:38
作者
Manteca, I [1 ]
Sotomayor, N [1 ]
Villa, MJ [1 ]
Lete, E [1 ]
机构
[1] UNIV BASQUE COUNTRY, FAC CIENCIAS, DEPT QUIM ORGAN, BILBAO 48080, SPAIN
关键词
D O I
10.1016/0040-4039(96)01745-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sequential carbophilic addition of organolithium reagents-N-acyliminium ion cyclization of N-phenenethylsuccinimide 3 yields pyrrolo[2,1-a]isoquinolones 1 in high yields, with the possibility of varying the substituent at C-10b by changing the organolithium. Application of this methodology to the cis-norbor-5-en-2,3-dicarboximide 7 using a functionalized organolithium reagent, the 3-(2-trimethylsilyl-1,3-dithian-2-yl)propyllithium 11, followed by desilylation and subsequent retro-Diels-Alder reaction affords the alpha,beta-unsaturated pyrroloisoquinolone 9b, immediate precursor of Erythrina-type alkaloids. Copyright (C) 1996 Published by Elsevier Science Ltd
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页码:7841 / 7844
页数:4
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