A STEREOCONTROLLED APPROACH TO 1-BETA-METHYLCARBAPENEM

被引:33
作者
DAVIES, SG [1 ]
HEDGECOCK, CJR [1 ]
MCKENNA, JM [1 ]
机构
[1] ROUSSEL LABS LTD,SWINDON SN3 5BZ,WILTS,ENGLAND
关键词
D O I
10.1016/0957-4166(95)00079-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Conjugate addition of lithium N-allyl-N-alpha-methylbenzylamide to chiral alpha,beta-unsaturated esters is subject to double stereodifferentiation, the mismatched pair reaction allowing access to an intermediate for 1 beta-methylcarbapenem synthesis.
引用
收藏
页码:827 / 830
页数:4
相关论文
共 25 条
[1]   DIASTEREOSELECTIVE ROUTES TO A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE - SCOPE OF ATE COMPLEX-FORMATION BETWEEN ESTER ENOLATES AND ORGANOBORANES AND ORGANOALANES [J].
BENDER, DR ;
DEMARCO, AM ;
MELILLO, DG ;
RISEMAN, SM ;
SHINKAI, I .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2411-2418
[2]   NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .2. TOTAL SYNTHESIS OF 8-OXO-4-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACIDS [J].
BRYAN, DB ;
HALL, RF ;
HOLDEN, KG ;
HUFFMAN, WF ;
GLEASON, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) :2353-2355
[3]  
DAVIES SG, 1995, IN PRESS J CHEM SOC
[4]   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
[5]   CHELATION CONTROLLED ALDOL ADDITIONS OF THE ENOLSILANE DERIVED FROM TERT-BUTYL THIOACETATE - A STEREOSELECTIVE APPROACH TO 1-BETA-METHYLTHIENAMYCIN [J].
GENNARI, C ;
COZZI, PG .
TETRAHEDRON, 1988, 44 (18) :5965-5974
[6]   1-BETA-METHYLTHIENAMYCIN - SOME STEREOCONTROLLED APPROACHES TOWARDS THE KEY INTERMEDIATE [J].
GURJAR, MK ;
BHANU, MN ;
KHARE, VB ;
BHANDARI, A ;
DESHMUKH, MN ;
RAO, AVR .
TETRAHEDRON, 1991, 47 (34) :7117-7128
[7]   AN ASYMMETRIC AMMONIA SYNTHON FOR MICHAEL ADDITIONS [J].
HAWKINS, JM ;
LEWIS, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2114-2121
[8]   ACYCLIC STEREOSELECTION .11. DOUBLE STEREO-DIFFERENTIATION AS A METHOD FOR ACHIEVING SUPERIOR CRAMS RULE SELECTIVITY IN ALDOL CONDENSATIONS WITH CHIRAL ALDEHYDES [J].
HEATHCOCK, CH ;
WHITE, CT ;
MORRISON, JJ ;
VANDERVEER, D .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1296-1309
[9]   ACYCLIC STEREOSELECTION .12. DOUBLE STEREODIFFERENTIATION WITH MUTUAL KINETIC RESOLUTION - A SUPERIOR CLASS OF REAGENTS FOR CONTROL OF CRAMS RULE STEREOSELECTION IN SYNTHESIS OF ERYTHRO-ALPHA-ALKYL-BETA-HYDROXY CARBOXYLIC-ACIDS FROM CHIRAL ALDEHYDES [J].
HEATHCOCK, CH ;
PIRRUNG, MC ;
LAMPE, J ;
BUSE, CT ;
YOUNG, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) :2290-2300
[10]   SYNTHESIS OF THE BETA-LACTAM ANTIBIOTIC (+)-THIENAMYCIN VIA AN INTERMEDIATE PI-ALLYLTRICARBONYLIRON LACTONE COMPLEX [J].
HODGSON, ST ;
HOLLINSHEAD, DM ;
LEY, SV .
TETRAHEDRON, 1985, 41 (24) :5871-5878