BETA-LACTAMS .1. HIGHLY DIASTEREOSELECTIVE ALKYLATION OF 4-ACETOXYAZETIDIN-2-ONE USEFUL FOR 1-BETA-METHYLCARBAPENEM SYNTHESIS

被引：40

作者：

NAGAO, Y

KUMAGAI, T

NAGASE, Y

TAMAI, S

INOUE, Y

SHIRO, M

机构：

[1] LEDERLE JAPAN LTD,CHEM & FORMULAT LABS,SHIKI,SAITAMA 353,JAPAN

[2] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 15期

关键词：

D O I：

10.1021/jo00041a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On the basis of the principle of hard and soft acids and bases, a highly diastereoselective ''asymmetric soft acid-soft base imine alkylation'' was developed. 4-Acetoxyazetidin-2-one (5) was alkylated with the tin(II) enolates of 3-acyl-(4S)-ethyl(and isopropyl)-1,3-thiazolidine-2-thiones 7a,b and 21a,b. The resultant alkylation products (9a,b and 24a,b) could be converted to 17, the key intermediate for the syntheses of both thienamycin (2) and imipenem (3), and to 35, the key intermediate for the synthesis of 1-beta-methylcarbapenem.

引用

收藏

页码：4232 / 4237

页数：6

相关论文

共 55 条

[11] CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA .

TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144

[12] LEWIS ACID MEDIATED CONDENSATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF CHIRAL CARBAPENEM PRECURSORS [J].

FUENTES, LM ;

SHINKAI, I ;

SALZMANN, TN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4675-4676

[13] A STEREOCONTROLLED SYNTHESIS OF AN IMPORTANT INTERMEDIATE FOR THE PREPARATION OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS [J].

FUENTES, LM ;

SHINKAI, I ;

KING, A ;

PURICK, R ;

REAMER, RA ;

SCHMITT, SM ;

CAMA, L ;

CHRISTENSEN, BG .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2563-2567

[14] FROM PENICILLIN TO PENEM AND CARBAPENEM .6. SYNTHESIS OF DETHIATHIENAMYCIN [J].

FUJIMOTO, K ;

IWANO, Y ;

HIRAI, K .

TETRAHEDRON LETTERS, 1985, 26 (01) :89-92

[15] STEREO-CONTROLLED AND ENANTIO-CONTROLLED SYNTHESIS OF CHIRAL INTERMEDIATES FOR THE TOTAL SYNTHESIS OF THIENAMYCIN AND RELATED BETA-LACTAM ANTIBIOTICS FROM 3-HYDROXYBUTYRATES [J].

GEORG, GI ;

GILL, HS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1433-1435

[16] STUDIES ON 1-CARBADETHIACEPHEMS .1. SYNTHESIS OF 1-CARBADETHIA-2-OXOCEPHEM 4-CARBOXYLATE [J].

GREENGRASS, CW ;

HOOPLE, DWT .

TETRAHEDRON LETTERS, 1981, 22 (52) :5335-5338

[17] STUDIES ON 1-CARBADETHIACEPHEMS .2. REACTION OF 4-ACETOXY-2-AZETIDINONE WITH ALUMINUM ENOLATES [J].

GREENGRASS, CW ;

NOBBS, MS .

TETRAHEDRON LETTERS, 1981, 22 (52) :5339-5340

[18] N-TRIMETHYLSILYL IMINES - APPLICATIONS TO THE SYNTHESIS OF BETA-LACTAMS [J].

HA, DC ;

HART, DJ ;

YANG, TK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :4819-4825

[19] A STEREOSELECTIVE APPROACH TO 1-BETA-METHYLCARBAPENEM ANTIBIOTIC STARTING FROM (R)-(-)-3-HYDROXYBUTYRIC ACID ESTER [J].

HATANAKA, M .

TETRAHEDRON LETTERS, 1987, 28 (01) :83-86

[20] FROM PENICILLIN TO PENEM AND CARBAPENEM .3. C1-UNIT INTRODUCTION AT C-4 POSITION OF AZETIDINONE [J].

HIRAI, K ;

IWANO, Y ;

FUJIMOTO, K .

TETRAHEDRON LETTERS, 1982, 23 (39) :4025-4026

← 1 2 3 4 5 6 →