Synthesis of indolizidines (-)-195B, (-)-223AB and (-)-239AB:: (2S,5R)-1-[(benzyloxy)carbonyl]-2-methoxycarbonyl-5-(4-pentenyl)pyrrolidine as a versatile chiral building block

被引:32
作者
Célimène, C [1 ]
Dhimane, H [1 ]
Lhommet, G [1 ]
机构
[1] Univ Pierre & Marie Curie, Lab Chim Heterocycles, UMR 7611, F-75252 Paris, France
关键词
D O I
10.1016/S0040-4020(98)00498-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total syntheses of three levogyre 3,5-disubstituted indolizidines, (-) 195B, (-)-223AB and (-)-239AB are described. The employed strategy is based on the utilization of the common enantiopure trans 2,5-disubstituted pyrrolidine 3, which is assembled by addition of pent-4-enylcopper to N-acyl iminium ion derived from (S)-proline. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:10457 / 10468
页数:12
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