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

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 43期

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

引用

页码：7841 / 7844

页数：4

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