Recent advances in the stereoselective synthesis of trans-3,4-disubstituted-piperidines:: applications to (-)-paroxetine

被引：80

作者：

De Risi, Carmela ^{[1
]}

Fanton, Giulia ^{[1
]}

Pollini, Gian P. ^{[1
]}

Trapella, Claudio ^{[1
]}

Valente, Filippo ^{[1
]}

Zanirato, Vinicio ^{[1
]}

机构：

[1] Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 02期

关键词：

D O I：

10.1016/j.tetasy.2008.01.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Piperidine ring systems are the key structural elements in a vast array of natural products as well as in a large class of biologically active natural products, being also often embedded within scaffolds recognized as privileged structures by medicinal chemists. Accordingly, new stereoselective routes to substituted piperidines are of widespread interest. An overview of the asymmetric synthetic routes to trans-3 4-disubstituted piperidines, featuring the substitution pattern of (-)-paroxetine [(3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine], a well-known selective serotonin reuptake inhibitor (SSRI) used worldwide as an antidepressant in humans, is presented. This review is mainly focused on the enantioselective routes to (-)-paroxetine, which has become a very popular synthetic target to test the efficiency of new methodologies. Some recent stereoselective approaches to the racemic compound are also included. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：131 / 155

页数：25

共 89 条

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