A HIGHLY STEREOSELECTIVE SYNTHESIS OF A KEY INTERMEDIATE OF 1-BETA-METHYLCARBAPENEMS EMPLOYING THE REFORMATSKY REACTION OF 3-(2-BROMOPROPIONYL)-2-OXAZOLIDONE DERIVATIVES

被引：46
作者：
ITO, Y [1 ]
TERASHIMA, S [1 ]
机构：
[1] SAGAMI CHEM RES CTR,NISHI OHNUMA,SAGAMIHARA,KANAGAWA 229,JAPAN
来源：
TETRAHEDRON LETTERS | 1987年 / 28卷 / 52期
关键词：
D O I：
10.1016/S0040-4039(00)96930-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
引用
收藏
页码：6625 / 6628
页数：4
相关论文
共 18 条
[1]  
AMOUROUX R, 1981, SYNTHESIS-STUTTGART, P270
[2]   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
[3]   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
[4]   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
[5]   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
[6]   A NEW SYNTHETIC STRATEGY FOR THE PENEMS - TOTAL SYNTHESIS OF (5R,6S,8R)-6-(ALPHA-HYDROXYETHYL)-2-(HYDROXYMETHYL)PENEM-3-CARBOXYLIC ACID [J].
HANESSIAN, S ;
BEDESCHI, A ;
BATTISTINI, C ;
MONGELLI, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1438-1439
[7]   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
[8]   SIMPLE, STEREOCONTROLLED SYNTHESIS OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM 3(R)-HYDROXYBUTYRIC ACID [J].
IIMORI, T ;
SHIBASAKI, M .
TETRAHEDRON LETTERS, 1986, 27 (19) :2149-2152
[9]   A NOVEL SYNTHESIS OF (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE, THE VERSATILE KEY INTERMEDIATE OF CARBAPENEM SYNTHESIS, FROM (S)-ETHYL LACTATE [J].
ITO, Y ;
KAWABATA, T ;
TERASHIMA, S .
TETRAHEDRON LETTERS, 1986, 27 (47) :5751-5754
[10]   A NOVEL AND EFFICIENT SYNTHESIS OF THE KEY INTERMEDIATE OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM (S)-METHYL 3-HYDROXY-2-METHYLPROPIONATE [J].
KAWABATA, T ;
KIMURA, Y ;
ITO, Y ;
TERASHIMA, S ;
SASAKI, A ;
SUNAGAWA, M .
TETRAHEDRON LETTERS, 1986, 27 (51) :6241-6244
12