TOTAL SYNTHESIS OF ANTIBIOTIC HYGROMYCIN-A

被引:96
作者
CHIDA, N [1 ]
OHTSUKA, M [1 ]
NAKAZAWA, K [1 ]
OGAWA, S [1 ]
机构
[1] KEIO UNIV,FAC SCI & TECHNOL,DEPT APPL CHEM,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN
关键词
D O I
10.1021/jo00009a009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the antibiotic (-)-hygromycin A (1) has been achieved by a coupling reaction of the sugar moiety (2) and the cyclitol moiety (3). Both components were synthesized in homochiral forms starting from D-glucose. This synthesis fully confirmed the unique structure of 1, which is much different from other usual aminocyclitol antibiotics.
引用
收藏
页码:2976 / 2983
页数:8
相关论文
共 33 条
  • [2] FUNCTIONALIZED CARBOCYCLES FROM CARBOHYDRATES .8. UNSATURATED CARBOHYDRATES .28. OBSERVATIONS ON THE CONVERSION OF 6-DEOXYHEX-5-ENOPYRANOSYL COMPOUNDS INTO 2-DEOXYINOSOSE DERIVATIVES
    BLATTNER, R
    FERRIER, RJ
    HAINES, SR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2413 - 2416
  • [3] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES
    BOCK, K
    PEDERSEN, C
    [J]. ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 : 27 - 66
  • [4] REACTION OF CYCLOHEXANE-1,2-DIOLS AND METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCO- AND GALACTO-PYRANOSIDE WITH METHYLENE HALIDES
    BRIMACOMBE, JS
    FOSTER, AB
    JONES, BD
    WILLARD, JJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (22): : 2404 - +
  • [5] TOTAL SYNTHESIS OF HYGROMYCIN-A
    CHIDA, N
    OHTSUKA, M
    NAKAZAWA, K
    OGAWA, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) : 436 - 438
  • [6] SYNTHESIS OF 2-ACETOXY-4-FORMYLPHENYL 2,3-DI-O-ACETYL-6-DEOXY-BETA-D-ARABINO-5-HEXULOFURANOSIDE, STRUCTURE CONFIRMATION OF THE ANOMERIC CONFIGURATION OF ANTIBIOTIC HYGROMYCIN-A
    CHIDA, N
    OHTSUKA, M
    OGAWA, S
    [J]. CHEMISTRY LETTERS, 1988, (06) : 969 - 972
  • [7] TOTAL SYNTHESIS OF METHOXYHYGROMYCIN AND ITS 5-EPIMER
    CHIDA, N
    NAKAZAWA, K
    OHTSUKA, M
    SUZUKI, M
    OGAWA, S
    [J]. CHEMISTRY LETTERS, 1990, (03) : 423 - 426
  • [8] COX DA, 1977, TOPICS ANTIBIOTIC CH, V1, P5
  • [9] UNSATURATED CARBOHYDRATES .21. CARBOCYCLIC RING-CLOSURE OF A HEX-5-ENOPYRANOSIDE DERIVATIVE
    FERRIER, RJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06): : 1455 - 1458
  • [10] PRACTICAL SYNTHESIS OF PARA-NITROPHENYL BETA-D-MANNOPYRANOSIDE
    GAREGG, PJ
    IVERSEN, T
    NORBERG, T
    [J]. CARBOHYDRATE RESEARCH, 1979, 73 (AUG) : 313 - 314