ENANTIOSELECTIVE ROUTES TOWARD 1-BETA-METHYLCARBAPENEMS FROM CHIRAL AZIRIDINES

被引:56
作者
TANNER, D
HE, HM
机构
[1] Department of Organic Chemistry, University of Uppsala, S-751 21 Uppsala
关键词
1-BETA-METHYLCARBAPENEMS; CHIRAL AZIRIDINES; REGIOSELECTIVE RING-OPENING;
D O I
10.1016/S0040-4020(01)89856-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes two enantioselective aziridine-based routes toward 1-beta-methylthienamycin, 2, and related carbapenems, the key steps being completely regioselective ring-opening reactions of the chiral aziridines 7 and 10 with AlMe3.
引用
收藏
页码:6079 / 6086
页数:8
相关论文
共 25 条
  • [1] STRUCTURE AND ABSOLUTE-CONFIGURATION OF THIENAMYCIN
    ALBERSSCHONBERG, G
    ARISON, BH
    HENSENS, OD
    HIRSHFIELD, J
    HOOGSTEEN, K
    KACZKA, EA
    RHODES, RE
    KAHAN, JS
    KAHAN, FM
    RATCLIFFE, RW
    WALTON, E
    RUSWINKLE, LJ
    MORIN, RB
    CHRISTENSEN, BG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) : 6491 - 6499
  • [2] THIENAMYCIN TOTAL SYNTHESIS - STEREOCONTROLLED INTRODUCTION OF THE HYDROXYETHYL SIDE-CHAIN
    BOUFFARD, FA
    CHRISTENSEN, BG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) : 2208 - 2212
  • [3] REDUCTIVE CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY DIISOBUTYLALUMINUM HYDRIDE
    COREY, EJ
    JONES, GB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) : 1028 - 1029
  • [4] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
    DALE, JA
    DULL, DL
    MOSHER, HS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
  • [5] A STEREOCONTROLLED SYNTHESIS OF AN IMPORTANT INTERMEDIATE FOR THE PREPARATION OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS
    FUENTES, LM
    SHINKAI, I
    KING, A
    PURICK, R
    REAMER, RA
    SCHMITT, SM
    CAMA, L
    CHRISTENSEN, BG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) : 2563 - 2567
  • [6] GEORG GI, 1989, STUDIES NATURAL PROD, V4
  • [7] 1-BETA-METHYLTHIENAMYCIN - SOME STEREOCONTROLLED APPROACHES TOWARDS THE KEY INTERMEDIATE
    GURJAR, MK
    BHANU, MN
    KHARE, VB
    BHANDARI, A
    DESHMUKH, MN
    RAO, AVR
    [J]. TETRAHEDRON, 1991, 47 (34) : 7117 - 7128
  • [8] A NOVEL RING-CLOSURE STRATEGY FOR THE CARBAPENEMS - THE TOTAL SYNTHESIS OF (+)-THIENAMYCIN
    HANESSIAN, S
    DESILETS, D
    BENNANI, YL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3098 - 3103
  • [9] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES
    HENRY, JR
    MARCIN, LR
    MCINTOSH, MC
    SCOLA, PM
    HARRIS, GD
    WEINREB, SM
    [J]. TETRAHEDRON LETTERS, 1989, 30 (42) : 5709 - 5712
  • [10] VERRUCARINS AND RORIDINS .40. SYNTHESES OF OPTICALLY-ACTIVE VERRUCARINIC ACID
    HEROLD, P
    MOHR, P
    TAMM, C
    [J]. HELVETICA CHIMICA ACTA, 1983, 66 (03) : 744 - 754