Highly stereocontrolled synthesis of a novel tribactam by reaction of an ester enolate with a N-trimethylsilylimine.

被引:20
作者
Camerini, R
Panunzio, M
Bonanomi, G
Donati, D
Perboni, A
机构
[1] CNR,CTR STUDIO FIS MACROMOLEC,DIPARTIMENTO CHIM G CIAMICIAN,I-40126 BOLOGNA,ITALY
[2] GLAXO SPA,RES LABS,I-37100 VERONA,ITALY
关键词
D O I
10.1016/0040-4039(96)00394-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The azetidinone 14, a key intermediate in the synthesis of novel tribactam antibiotics (e.g. 2) was obtained via condensation of an ester enolate with a N-trimethylsilylimine. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:2467 / 2470
页数:4
相关论文
共 33 条
  • [1] SYNTHESIS OF CARBAPENEMS VIA METALLOIMINES-ESTER ENOLATES CONDENSATION - A NEW SYNTHESIS OF (+)-1-BETA-METHYL PS-5
    BANDINI, E
    CAINELLI, G
    GIACOMINI, D
    MARTELLI, G
    PANUNZIO, M
    SPUNTA, G
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) : 2347 - 2350
  • [2] BANDINI E, 1993, GAZZ CHIM ITAL, V123, P509
  • [3] BANDINI E, 1993, SEMINARS ORGANIC SYN, P47
  • [4] THE SYNTHESIS OF A KEY INTERMEDIATE OF TRICYCLIC BETA-LACTAM ANTIBIOTICS
    BISMARA, C
    DIFABIO, R
    DONATI, D
    ROSSI, T
    THOMAS, RJ
    [J]. TETRAHEDRON LETTERS, 1995, 36 (24) : 4283 - 4286
  • [5] SYNTHESIS OF (1S,2S)-PHOSPHOTHREONINE VIA N-TRIMETHYLSILYLIMINE OF (S)-LACTIC ALDEHYDE
    BONGINI, A
    CAMERINI, R
    HOFMAN, S
    PANUNZIO, M
    [J]. TETRAHEDRON LETTERS, 1994, 35 (43) : 8045 - 8048
  • [6] A NEW APPROACH TO THE DIASTEREOSELECTIVE SYNTHESIS OF ALDOLS - INTRODUCTION OF THE 6-ALPHA-(1R-HYDROXYETHYL)SIDE CHAIN OF THE CARBAPENEM AND PENEM ANTIBIOTICS
    BOUFFARD, FA
    SALZMANN, TN
    [J]. TETRAHEDRON LETTERS, 1985, 26 (51) : 6285 - 6288
  • [7] BROWN MJ, 1989, HETEROCYCLES, V29, P2225
  • [8] BETA-LACTAMS FROM ESTER ENOLATES AND N-TMSIMINES - ENANTIOSELECTIVE SYNTHESIS OF (6R,7S)-1-BETA-3-DIMETHYL-3-ISOCEPHEM
    CAINELLI, G
    PANUNZIO, M
    BANDINI, E
    MARTELLI, G
    SPUNTA, G
    DACOL, M
    [J]. TETRAHEDRON, 1995, 51 (17) : 5067 - 5072
  • [9] CAINELLI G, 1996, TETRAHEDRON, P52
  • [10] CAINELLI G, 1995, IN PRESS CHEM SYNTHE