A practical enzymatic procedure for the resolution of N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-one

被引:35
作者
Mahmoudian, M [1 ]
Lowdon, A [1 ]
Jones, M [1 ]
Dawson, M [1 ]
Wallis, C [1 ]
机构
[1] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1016/S0957-4166(99)00091-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A simple and efficient process for the enantioselective resolution of N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-one has been developed using commercially available hydrolytic enzymes. This offers a practical approach for the preparation of enantiomerically pure N-substituted gamma-lactams. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1201 / 1206
页数:6
相关论文
共 13 条
[1]  
[Anonymous], 1997, BIOTECHNOLOGY ANTIBI
[2]  
Boehme R. E., 1994, Antiviral Research, V23, P97
[3]   SYNTHESIS AND ENZYMATIC RESOLUTION OF CARBOCYCLIC 2'-ARA-FLUORO-GUANOSINE - A POTENT NEW ANTI-HERPETIC AGENT [J].
BORTHWICK, AD ;
BUTT, S ;
BIGGADIKE, K ;
EXALL, AM ;
ROBERTS, SM ;
YOUDS, PM ;
KIRK, BE ;
BOOTH, BR ;
CAMERON, JM ;
COX, SW ;
MARR, CLP ;
SHILL, MD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :656-658
[4]   (+/-) 4-BETA-AMINO-2-ALPHA,3-ALPHA-DIHYDROXY-1-BETA-CYCLOPENTANEMETHANOL HYDROCHLORIDE - CARBOCYCLIC RIBOFURANOSYLAMINE FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].
CERMAK, RC ;
VINCE, R .
TETRAHEDRON LETTERS, 1981, 22 (25) :2331-2332
[5]   CARBOVIR - THE (-) ENANTIOMER IS A POTENT AND SELECTIVE ANTIVIRAL AGENT AGAINST HUMAN-IMMUNODEFICIENCY-VIRUS INVITRO [J].
COATES, JAV ;
INGGALL, HJ ;
PEARSON, BA ;
PENN, CR ;
STORER, R ;
WILLIAMSON, C ;
CAMERON, JM .
ANTIVIRAL RESEARCH, 1991, 15 (02) :161-168
[6]  
Daluge S. M., 1991, EP, Patent No. [434,450, 434450]
[7]  
DAWSON MJ, 1999, Patent No. 9805291
[8]   POTENTIAL USE OF CARBOCYCLIC NUCLEOSIDES FOR THE TREATMENT OF AIDS - CHEMOENZYMATIC SYNTHESES OF THE ENANTIOMERS OF CARBOVIR [J].
EVANS, CT ;
ROBERTS, SM ;
SHOBERU, KA ;
SUTHERLAND, AG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :589-592
[9]  
Evans CT, 1991, Eur. Pat. Appl., Patent No. [0424 064 B1, 0424064]
[10]   SYNTHESIS FROM (-)-ARISTEROMYCIN AND X-RAY STRUCTURE OF (-)-CARBOVIR [J].
EXALL, AM ;
JONES, MF ;
MO, CL ;
MYERS, PL ;
PATERNOSTER, IL ;
SINGH, H ;
STORER, R ;
WEINGARTEN, GG ;
WILLIAMSON, C ;
BRODIE, AC ;
COOK, J ;
LAKE, DE ;
MEERHOLZ, CA ;
TURNBULL, PJ ;
HIGHCOCK, RM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10) :2467-2477