CHEMOENZYMATIC ENANTIOSELECTIVE SYNTHESIS OF AMIDINOMYCIN

被引：15

作者：

CHENEVERT, R

LAVOIE, M

COURCHESNE, G

MARTIN, R

机构：

来源：

CHEMISTRY LETTERS | 1994年 / 01期

关键词：

D O I：

10.1246/cl.1994.93

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the first asymmetric synthesis of amidinomycin, an antiviral antibiotic metabolite. Amidinomycin of high enantiomeric purity (ee 91%) was prepared from norbornylene in 8 steps. The key step is an enzymatic discrimination of enantiotopic groups in meso cis-1,3-dicarbomethoxycyclopentane or in meso cis-cyclopentane-1,3-dicarboxylic acid anhydride.

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页码：93 / 96

页数：4

相关论文

共 19 条

[1] SYNTHESIS OF ANALOGS OF GABA .3. ALL 4 STEREOISOMERS OF 3-AMINOCYCLOPENTANECARBOXYLIC ACID AND A STEREOCHEMICAL CORRELATION WITH AMIDINOMYCIN [J].

ALLAN, RD ;

JOHNSTON, GAR ;

TWITCHIN, B .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (11) :2517-2521

[2] SYNTHESIS OF EPIMERIC 3-AMINOCYCLOPENTANE CARBOXYLIC ACIDS [J].

BERGER, H ;

PAUL, H ;

HILGETAG, G .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (05) :1525-&

[3] HIGHLY REGIOSELECTIVE RING-OPENING OF ALPHA-SUBSTITUTED CYCLIC ACID ANHYDRIDES CATALYZED BY LIPASE [J].

HIRATAKE, J ;

YAMAMOTO, K ;

YAMAMOTO, Y ;

ODA, J .

TETRAHEDRON LETTERS, 1989, 30 (12) :1555-1556

[4] ENZYMES IN ORGANIC-SYNTHESIS .33. STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSES OF MESO-CYCLOPENTYL-1,3-DIESTERS, TETRAHYDROFURANYL-1,3-DIESTERS, AND TETRAHYDROTHIOPHENYL-1,3-DIESTERS [J].

JONES, JB ;

HINKS, RS ;

HULTIN, PG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (02) :452-456

[5]

KANEDA M, 1980, J ANTIBIOT, V23, P778

[6] CRYSTAL-STRUCTURE AND MOLECULAR MODELING OF THE ANTIMICROBIAL DRUG PENTAMIDINE [J].

LOWE, PR ;

SANSOM, CE ;

SCHWALBE, CH ;

STEVENS, MFG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) :1164-1165

[7] NOVEL LINKED ANTIVIRAL AND ANTITUMOR AGENTS RELATED TO NETROPSIN AND DISTAMYCIN - SYNTHESIS AND BIOLOGICAL EVALUATION [J].

LOWN, JW ;

KROWICKI, K ;

BALZARINI, J ;

NEWMAN, RA ;

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2368-2375

[8]

NAKAMURA S, 1961, CHEM PHARM BULL, V9, P641

[9]

NAKAMURA S, 1961, J ANTIBIOT, V14, P163

[10]

NAKAMURA S, 1961, J ANTIBIOT, V14, P103