NEW SYNTHESIS OF 4-ACETOXY-2-AZETIDINONES BY USE OF ELECTROCHEMICAL OXIDATION

被引：38

作者：

MORI, M

KAGECHIKA, K

SASAI, H

SHIBASAKI, M

机构：

[1] Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo

来源：

TETRAHEDRON | 1991年 / 47卷 / 4-5期

关键词：

D O I：

10.1016/S0040-4020(01)87042-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Acetoxy-2-azetidinone was synthesized from 4-carboxy-2-azetidinone by Kolbe-type electrolysis. Optically pure -acetoxy-3-[1-(t-butyldimethylsiloxy)ethyl]-2-azetidinone, which is an important intermediate for the synthesis of thienamycin, and (+)-PS-5 were synthesized by use of this method.

引用

收藏

页码：531 / 540

页数：10

相关论文

共 32 条

[1] SYNTHESIS OF AN OPTICALLY-ACTIVE PENEM INTERMEDIATE BY ASYMMETRIC AMIDOALKYLATION [J].

ALLMENDINGER, T ;

RIHS, G ;

WETTER, H .

HELVETICA CHIMICA ACTA, 1988, 71 (02) :395-403

[2] ALDOL CONDENSATIONS OF REGIOSPECIFIC PENICILLANATE AND CEPHALOSPORANATE ENOLATES - HYDROXYETHYLATION AT C-6 AND C-7 [J].

DININNO, F ;

BEATTIE, TR ;

CHRISTENSEN, BG .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (18) :2960-2965

[3] ACYLOXYLATION AT THE 4-POSITION OF AZETIDIN-2-ONES [J].

EASTON, CJ ;

LOVE, SG ;

WANG, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02) :277-282

[4] DIRECT INTRODUCTION OF A BENZOYLOXY SUBSTITUENT AT THE C-4 POSITION OF BETA-LACTAMS [J].

EASTON, CJ ;

LOVE, SG .

TETRAHEDRON LETTERS, 1986, 27 (20) :2315-2318

[5]

ELLENBERGER FM, 1987, SYNTHESIS-STUTTGART, P324

[6] A FACILE SYNTHESIS OF TRANS (+)-4-CARBOXYMETHYL-3-ETHYLAZETIDIN-2-ONE AND ITS CONVERSION INTO NATURAL PS-5 [J].

FAVARA, D ;

OMODEISALE, A ;

CONSONNI, P ;

DEPAOLI, A .

TETRAHEDRON LETTERS, 1982, 23 (30) :3105-3108

[7] AN ASYMMETRIC-SYNTHESIS OF CARBAPENEM ANTIBIOTIC (+)-PS-5 FROM ETHYL 3-HYDROXYBUTANOATE [J].

GEORG, GI ;

KANT, J .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :692-695

[8] SYNTHESIS OF OPTICALLY-ACTIVE PENEMS [J].

GIRIJAVALLABHAN, VM ;

GANGULY, AK ;

MCCOMBIE, SW ;

PINTO, P ;

RIZVI, R .

TETRAHEDRON LETTERS, 1981, 22 (36) :3485-3488

[9] FROM PENICILLIN TO PENEM AND CARBAPENEM .1. RACEMIZATION OF 6,6-DIBROMO SECOPENICILLIN, AND SYNTHESIS OF 2-OXO PENAM DERIVATIVE [J].

HIRAI, K ;

IWANO, Y ;

FUJIMOTO, K .

HETEROCYCLES, 1982, 17 :201-207

[10] ON THE STEREOCHEMICAL COURSE OF VINYLOXYBORANE IMINE CONDENSATION - THE STEREOSELECTIVE FORMATION OF THREO BETA-AMINO ACID-DERIVATIVES [J].

IIMORI, T ;

ISHIDA, Y ;

SHIBASAKI, M .

TETRAHEDRON LETTERS, 1986, 27 (19) :2153-2156

← 1 2 3 4 →