Ring expansion: formal total synthesis of (-)-paroxetine

被引:38
作者
Cossy, J
Mirguet, O
Pardo, DG
Desmurs, JR
机构
[1] Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, France
[2] Rhodia, F-69457 Lyon 06, France
关键词
D O I
10.1016/S0040-4039(01)01096-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A ring expansion and a radical dehalogenation have been used as the key steps in a formal total synthesis of (-)-paroxetine. A stereoselective ring expansion of prolinol generated the Substituted piperidine ring precursor of (-)-paroxetine. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5705 / 5707
页数:3
相关论文
共 34 条
[1]  
ADGER BM, 1997, Patent No. 9724323
[2]   Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].
Amat, M ;
Bosch, J ;
Hidalgo, J ;
Cantó, M ;
Pérez, M ;
Llor, N ;
Molins, E ;
Miravitlles, C ;
Orozco, M ;
Luque, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084
[3]   Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions [J].
Bailey, JH ;
Cherry, DT ;
Crapnell, KM ;
Moloney, MG ;
Shim, SB ;
Bamford, MJ ;
Lamont, RB .
TETRAHEDRON, 1997, 53 (34) :11731-11744
[4]   Enantioselective synthesis of 2,3-disubstituted piperidines from (S)-methylpyroglutamate [J].
Calvez, O ;
Chiaroni, A ;
Langlois, N .
TETRAHEDRON LETTERS, 1998, 39 (51) :9447-9450
[5]  
Christensen J. A., 1977, 4-Phenylpiperidine compounds, Patent No. [US4007196A, 4007196]
[6]  
Cossy J, 1999, EUR J ORG CHEM, V1999, P1693
[7]   A short and efficient synthesis of zamifenacin a muscarinic M-3 receptor antagonist [J].
Cossy, J ;
Dumas, C ;
Pardo, DG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (10) :1343-1344
[8]   FORMATION OF OPTICALLY-ACTIVE 3-HYDROXYPIPERIDINES [J].
COSSY, J ;
DUMAS, C ;
MICHEL, P ;
PARDO, DG .
TETRAHEDRON LETTERS, 1995, 36 (04) :549-552
[9]  
Cossy J, 1997, SYNLETT, P905
[10]  
Davis PW, 1998, BIOTECHNOL BIOENG, V61, P143, DOI 10.1002/(SICI)1097-0290(1998)61:3<143::AID-CC2>3.0.CO