A short formal synthesis of paroxetine. Diastereoselective cuprate addition to a chiral racemic olefinic amido ester

被引：24

作者：

Cossy, J

Mirguet, O

Pardo, DG

Desmurs, JR

机构：

[1] Ecole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, F-75231 Paris 05, France

[2] Rhodia, F-69457 Lyon 06, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(01)01666-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereoselective conjugate addition of an organocopper reagent to a chiral racemic olefinic amido ester has been used as the key step in a formal total synthesis of paroxetine. (C), 2001 Published by Elsevier Science Ltd.

引用

页码：7805 / 7807

页数：3

共 24 条

[1] ADGER BM, 1997, Patent No. 9724323
[2] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine
Amat, M
Bosch, J
Hidalgo, J
Cantó, M
Pérez, M
Llor, N
Molins, E
Miravitlles, C
Orozco, M
Luque, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 3074 - 3084
[3] Christensen J. A., 1977, 4-Phenylpiperidine compounds, Patent No. [US4007196A, 4007196]
[4] Ring expansion: formal total synthesis of (-)-paroxetine
Cossy, J
Mirguet, O
Pardo, DG
Desmurs, JR
[J]. TETRAHEDRON LETTERS, 2001, 42 (33) : 5705 - 5707
[5] Synthesis and 5HT modulating activity of stereoisomers of 3-phenoxymethyl-4-phenylpiperidines
Engelstoft, M
Hansen, JB
[J]. ACTA CHEMICA SCANDINAVICA, 1996, 50 (02): : 164 - 169
[6] Paroxetine - An update of its pharmacology and therapeutic use in depression and a review of its use in other disorders
Gunasekara, NS
Noble, S
Benfield, P
[J]. DRUGS, 1998, 55 (01) : 85 - 120
[7] ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED ALCANOIC ACIDS VIA HIGHLY STEREOSELECTIVE CONJUGATE ADDITIONS OF ORGANOCOPPER COMPOUNDS TO CHIRAL ENOATES
HELMCHEN, G
WEGNER, G
[J]. TETRAHEDRON LETTERS, 1985, 26 (49) : 6051 - 6054
[8] IMBROISI DD, 1991, J CHEM SOC PERK T 1, P1815
[9] Highly diastereoselective and enantioselective carbon-carbon bond formations in conjugate additions of lithiated N-boc allylamines to nitroalkenes:: Enantioselective synthesis of 3,4-and 3,4,5-substituted piperidines including (-)-paroxetine
Johnson, TA
Curtis, MD
Beak, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (05) : 1004 - 1005
[10] Kreidl J., 1998, WO Patent, Patent No. 9801424

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