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.

引用

收藏

页码：93 / 96

页数：4

相关论文

共 19 条

[11] SYNTHESIS OF 2,4-DIMETHYLGLUTARIC ACID MONOESTERS VIA ENZYME-CATALYZED ASYMMETRIC ALCOHOLYSIS OF MESO-2,4-DIMETHYLGLUTARIC ANHYDRIDE [J].

OZEGOWSKI, R ;

KUNATH, A ;

SCHICK, H .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :695-698

[12] SYNTHESIS OF BETA-(BETA-ALANYLAMINO)-PROPIONAMIDINE AND CIS- AND TRANS-(+-)-AMIDINOMYCIN [J].

PAUL, H ;

BERGER, H ;

BOEDEN, H ;

HILGETAG, G .

ARCHIV DER PHARMAZIE, 1968, 301 (07) :512-&

[13] OZONOLYSIS OF NORBORNYLENE [J].

PERRY, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (06) :829-833

[14] SYNTHESIS OF NOVEL THIAZOLE-CONTAINING DNA MINOR GROOVE BINDING OLIGOPEPTIDES RELATED TO THE ANTIBIOTIC DISTAMYCIN [J].

RAO, KE ;

BATHINI, Y ;

LOWN, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :728-737

[15]

SERVI S, 1992, 1992 NATO ADV RES WO

[16] ANALOGS OF 1,5-BIS(4-AMIDINOPHENOXY)PENTANE (PENTAMIDINE) IN THE TREATMENT OF EXPERIMENTAL PNEUMOCYSTIS-CARINII PNEUMONIA [J].

TIDWELL, RR ;

JONES, SK ;

GERATZ, JD ;

OHEMENG, KA ;

CORY, M ;

HALL, JE .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (04) :1252-1257

[17] ASYMMETRIC RING-OPENING OF CYCLIC ACID ANHYDRIDES WITH LIPASE IN ORGANIC-SOLVENTS [J].

YAMAMOTO, K ;

NISHIOKA, T ;

ODA, J ;

YAMAMOTO, Y .

TETRAHEDRON LETTERS, 1988, 29 (14) :1717-1720

[18] ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE 3-SUBSTITUTED DELTA-VALEROLACTONES USING LIPASE IN ORGANIC-SOLVENTS [J].

YAMAMOTO, Y ;

IWASA, M ;

SAWADA, S ;

ODA, J .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (12) :3269-3274

[19] ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE LACTONES FROM CYCLIC ACID ANHYDRIDES USING LIPASE IN ORGANIC-SOLVENTS [J].

YAMAMOTO, Y ;

YAMAMOTO, K ;

NISHIOKA, T ;

ODA, J .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1988, 52 (12) :3087-3092