SUBSTITUTION-REACTIONS OF 2-PHENYLSULFONYL-PIPERIDINES AND 2-PHENYLSULFONYL-PYRROLIDINES WITH CARBON NUCLEOPHILES - SYNTHESIS OF THE PYRROLIDINE ALKALOIDS NORRUSPOLINE AND RUSPOLINONE

被引：86

作者：

BROWN, DS ^{[1
]}

CHARREAU, P ^{[1
]}

HANSSON, T ^{[1
]}

LEY, SV ^{[1
]}

机构：

[1] IMPERIAL COLL SCI TECHNOL & MED, DEPT CHEM, S KENSINGTON, LONDON SW7 2AY, ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(01)86388-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several 2-phenylsuphonyl-piperidines and -pyrrolidines were prepared from the corresponding N-acyl animals by treatment with benzenesulphinic acid. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. Typical nucleophiles used in these studies were organometallic reagents derived from Grignard reagents and zinc halide together with silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilyl cyanide in the presence of a Lewis acid. These methods were employed in the synthesis of two natural product alkaloids; Norruspoline (38) and Ruspolinone (40).

引用

页码：1311 / 1328

页数：18

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