EFFICIENT SYNTHESIS OF CARBAPENEMS VIA THE OXALIMIDE CYCLIZATION - MANIPULATION OF PROTECTING GROUPS AT THE OXALIMIDE STAGE

被引:31
作者
KING, SA
PIPIK, B
THOMPSON, AS
DECAMP, A
VERHOEVEN, TR
机构
[1] Department of Process Research Merck Research Laboratories Rahway
关键词
D O I
10.1016/0040-4039(95)00854-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of the carbapenem nucleus from TBDMS protected acetoxyazetidinone via oxalimide cyclization technology is demonstrated. A key step is desilylation of the oxalimide intermediate. Access to a variety of protecting group schemes is demonstrated.
引用
收藏
页码:4563 / 4566
页数:4
相关论文
共 16 条
  • [1] NEW SYNTHESIS OF PENEMS, THE OXALIMIDE CYCLIZATION REACTION
    AFONSO, A
    HON, F
    WEINSTEIN, J
    GANGULY, AK
    MCPHAIL, AT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) : 6138 - 6139
  • [2] CONVENIENT SYNTHESIS OF ALPHA-(2-OXOAZETIDIN-4-YL) ESTERS AND KETONES AND RELATED SYSTEMS
    ATTRILL, RP
    BARRETT, AGM
    QUAYLE, P
    VANDERWESTHUIZEN, J
    BETTS, MJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) : 1679 - 1682
  • [3] STERICALLY HINDERED SILYL PERCHLORATES AS BLOCKING REAGENTS
    BARTON, TJ
    TULLY, CR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) : 3649 - 3653
  • [4] STRUCTURE-ACTIVITY-RELATIONSHIPS IN THE 2-ARYLCARBAPENEM SERIES - SYNTHESIS OF 1-METHYL-2-ARYLCARBAPENEMS
    GUTHIKONDA, RN
    CAMA, LD
    QUESADA, M
    WOODS, MF
    SALZMANN, TN
    CHRISTENSEN, BG
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (05) : 871 - 880
  • [5] HUBER J, 1994, 34TH INT C ANT AG CH
  • [6] KAHAN JS, 1979, J ANTIBIOT, V22, P1
  • [7] CLEAVAGE OF T-BUTYLDIMETHYLSILYL ETHERS WITH BORON-TRIFLUORIDE ETHERATE
    KELLY, DR
    ROBERTS, SM
    NEWTON, RF
    [J]. SYNTHETIC COMMUNICATIONS, 1979, 9 (04) : 295 - 299
  • [8] SYNTHESIS OF GLYCOPEPTIDES, PARTIAL STRUCTURES OF BIOLOGICAL RECOGNITION COMPONENTS
    KUNZ, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04): : 294 - 308
  • [9] NAGAHARA T, 1987, HETEROCYCLES, V25, P729
  • [10] THE CARBONYL-CARBONYL COUPLING ROUTE TO PENEMS - A STEPWISE ANALYSIS
    PERRONE, E
    ALPEGIANI, M
    BEDESCHI, A
    GIUDICI, F
    FRANCESCHI, G
    [J]. TETRAHEDRON LETTERS, 1984, 25 (22) : 2399 - 2402