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

[1] TRIFLUOROMETHYL SULFATES OF TIN [J].

BATCHELOR, RJ ;

RUDDICK, JNR ;

SAMS, JR ;

AUBKE, F .

INORGANIC CHEMISTRY, 1977, 16 (06) :1414-1417

[2] A VERSATILE SYNTHESIS OF CARBAPENEMS FROM SUBSTITUTED DIHYDROPYRANS [J].

BAYLES, R ;

FLYNN, AP ;

GALT, RHB ;

KIRBY, S ;

TURNER, RW .

TETRAHEDRON LETTERS, 1988, 29 (48) :6345-6348

[3]

BECKMANN E, 1889, LIEBIGS ANN CHEM, V250, P325

[4] C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS [J].

BROOKS, DW ;

LU, LDL ;

MASAMUNE, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :72-74

[5] STEREOCONTROLLED TOTAL SYNTHESIS OF THE CHIRAL BUILDING BLOCK (3S,4R)-3-[(R)-1-HYDROXYETHYL]-4-ACETYLOXY-AZETIDIN-2-ONE - A USEFUL SYNTHON FOR THE SYNTHESIS OF (+)-THIENAMYCIN, CARBAPENEMS AND PENEMS [J].

CAINELLI, G ;

CONTENTO, M ;

GIACOMINI, D ;

PANUNZIO, M .

TETRAHEDRON LETTERS, 1985, 26 (07) :937-940

[6] A FACILE, STEREOCONTROLLED ENTRY TO KEY INTERMEDIATES FOR THIENAMYCIN SYNTHESIS FROM ETHYL (S)-3-HYDROXYBUTANOATE [J].

CHIBA, T ;

NAGATSUMA, M ;

NAKAI, T .

CHEMISTRY LETTERS, 1985, (09) :1343-1346

[7]

CLAUSS K, 1974, LIEBIGS ANN CHEM, P539

[8] SIMPLE AND HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE INVOLVING DIVALENT TIN ENOLATES [J].

DEZIEL, R ;

FAVREAU, D .

TETRAHEDRON LETTERS, 1986, 27 (47) :5687-5690

[9] AN EXPEDITIOUS SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE [J].

DEZIEL, R ;

ENDO, M .

TETRAHEDRON LETTERS, 1988, 29 (01) :61-64

[10] 1-BETA-METHYLCARBAPENEM INTERMEDIATES .2. STEREOSELECTIVE SYNTHESIS OF (3S,4R)-3-[(1R)-1-TERT-BUTYLDIMETHYLSILYLOXYETHYL]-4-[(1R)-3-METHOXYCARBONYL-1-METHYL-2-OXOPROPYL]AZETIDIN-2-ONE AND ITS RELATED CHEMISTRY [J].

ENDO, M ;

DROGHINI, R .

CANADIAN JOURNAL OF CHEMISTRY, 1988, 66 (06) :1400-1404

← 1 2 3 4 5 6 →