A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

被引:35
作者
Song, CE
Lee, SW
Roh, EJ
Lee, SG
Lee, WK
机构
[1] Korea Inst Sci & Technol, Div Appl Sci, Seoul 130650, South Korea
[2] Sogang Univ, Dept Chem, Seoul 121742, South Korea
关键词
D O I
10.1016/S0957-4166(98)00049-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:983 / 992
页数:10
相关论文
共 56 条
[1]   A CHEMOENZYMATIC APPROACH TO CHIRAL PHENYLISOSERINATES USING 4-ISOPROPYL-2-OXAZOLIN-5-ONE AS MASKED UMPOLED SYNTHON FOR HYDROXYCARBONYL ANION [J].
BARCO, A ;
BENETTI, S ;
DERISI, C ;
POLLINI, GP ;
ROMAGNOLI, R ;
ZANIRATO, V .
TETRAHEDRON LETTERS, 1994, 35 (49) :9289-9292
[2]  
Beckwith A.L.J., 1970, CHEM AMIDES, P73
[3]   ASYMMETRIC DIHYDROXYLATION (AD) OF N,N-DIALKYL AND N-METHOXY-N-METHYL ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED AMIDES [J].
BENNANI, YL ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1993, 34 (13) :2079-2082
[4]  
BONINI C, 1994, CHEM COMMUN, P2767
[5]   ASYMMETRIC-SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE HYDROXYLATION OF HOMOCHIRAL BETA-AMINO ENOLATES [J].
BUNNAGE, ME ;
CHERNEGA, AN ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2373-2384
[6]   ASYMMETRIC-SYNTHESIS OF THE TAXOL AND TAXOTERE C-13 SIDE-CHAINS [J].
BUNNAGE, ME ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2385-2391
[7]  
Challis B.C., 1970, The Chemistry of Amides, P731, DOI [10.1002/9780470771235.ch13, DOI 10.1002/9780470771235.CH13]
[8]   TOTAL SYNTHESIS OF ALTEROBACTIN-A, A SUPER SIDEROPHORE FROM AN OPEN-OCEAN BACTERIUM [J].
DENG, JG ;
HAMADA, Y ;
SHIOIRI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (29) :7824-7825
[9]   AN EFFICIENT, ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN [J].
DENIS, JN ;
GREENE, AE ;
SERRA, AA ;
LUCHE, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) :46-50
[10]   A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL [J].
DENIS, JN ;
GREENE, AE ;
GUENARD, D ;
GUERITTEVOEGELEIN, F ;
MANGATAL, L ;
POTIER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5917-5919