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 [J].
BLATTNER, R ;
FERRIER, RJ ;
HAINES, SR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2413-2416
[3]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES [J].
BOCK, K ;
PEDERSEN, C .
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 [J].
BRIMACOMBE, JS ;
FOSTER, AB ;
JONES, BD ;
WILLARD, JJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (22) :2404-+
[5]   TOTAL SYNTHESIS OF HYGROMYCIN-A [J].
CHIDA, N ;
OHTSUKA, M ;
NAKAZAWA, K ;
OGAWA, S .
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 [J].
CHIDA, N ;
OHTSUKA, M ;
OGAWA, S .
CHEMISTRY LETTERS, 1988, (06) :969-972
[7]   TOTAL SYNTHESIS OF METHOXYHYGROMYCIN AND ITS 5-EPIMER [J].
CHIDA, N ;
NAKAZAWA, K ;
OHTSUKA, M ;
SUZUKI, M ;
OGAWA, S .
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 [J].
FERRIER, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1455-1458
[10]   PRACTICAL SYNTHESIS OF PARA-NITROPHENYL BETA-D-MANNOPYRANOSIDE [J].
GAREGG, PJ ;
IVERSEN, T ;
NORBERG, T .
CARBOHYDRATE RESEARCH, 1979, 73 (AUG) :313-314