Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization

被引:67
作者
Cutchins, WW [1 ]
McDonald, FE [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
关键词
D O I
10.1021/ol017195f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A stereoselective synthesis of the C-3 branched amino glycals of vancosamine and saccharosamine is described that features a tungsten carbonyl catalyzed cycloisomerization of the corresponding alkynyl alcohol.
引用
收藏
页码:749 / 752
页数:4
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共 29 条
[1]   THE SYNTHESIS OF SOME DERIVATIVES OF L-VANCOSAMINE (3-AMINO-2,3,6-TRIDEOXY-3-C-METHYL-L-LYXO-HEXOSE) [J].
AHMAD, HI ;
BRIMACOMBE, JS ;
MENGECH, AS ;
TUCKER, LCN .
CARBOHYDRATE RESEARCH, 1981, 93 (02) :288-293
[2]   BRANCHED-CHAIN SUGARS .19. THE SYNTHESIS OF A DERIVATIVE OF L-DECILONITROSE (2,3,6-TRIDEOXY-3-C-METHYL-3-NITRO-L-RIBO-HEXOSE) [J].
BRIMACOMBE, JS ;
RAHMAN, KMM .
CARBOHYDRATE RESEARCH, 1985, 140 (01) :163-166
[3]   BRANCHED-CHAIN SUGARS .14. AN APPROACH TO BRANCHED-CHAIN AMINO-SUGARS, PARTICULARLY DERIVATIVES OF L-VANCOSAMINE (3-AMINO-2,3,6-TRIDEOXY-3-C-METHYL-L-LYXO-HEXOSE) AND ITS D-ENANTIOMER, VIA THE CYANOHYDRIN ROUTE [J].
BRIMACOMBE, JS ;
MENGECH, AS ;
RAHMAN, KMM ;
TUCKER, LCN .
CARBOHYDRATE RESEARCH, 1982, 110 (02) :207-215
[4]   SYNTHESES OF BIOLOGICALLY IMPORTANT CARBOHYDRATES .20. N-ACETYL-1,4-DI-O-ACETYL-BETA-DL-VANCOSAMINE [J].
DYONG, I ;
FRIEGE, H .
CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (09) :3273-3281
[5]   Chelation-controlled reduction of α- and β-oxygenated ketones with lithium tri-n-butylborohydride. [J].
Faucher, AM ;
Brochu, C ;
Landry, SR ;
Duchesne, I ;
Hantos, S ;
Roy, A ;
Myles, A ;
Legault, C .
TETRAHEDRON LETTERS, 1998, 39 (46) :8425-8428
[6]  
GEORG GI, 1993, ORGANIC CHEM BETA LA, P256
[7]  
GIOVANNI F, 1981, TETRAHEDRON LETT, V22, P5073
[8]   A NEW STEREOSELECTIVE ROUTE TO BRANCHED-CHAIN NITRO AND AMINO-SUGARS - SYNTHESIS OF BOTH ENANTIOMERS OF DECILONITROSE AND AVIDINOSAMINE [J].
GREVEN, R ;
JUTTEN, P ;
SCHARF, HD .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3742-3747
[9]   STEREOSELECTIVE SYNTHESIS OF L-VANCOSAMINE METHYL BETA-GLYCOSIDE BY ADDITION OF AN ORGANOCERIUM REAGENT TO O-BENZYLOXIME ETHERS [J].
GREVEN, R ;
JUTTEN, P ;
SCHARF, HD .
CARBOHYDRATE RESEARCH, 1995, 275 (01) :83-93
[10]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .50. A STEREOSELECTIVE SYNTHESIS OF A DERIVATIVE OF L-VANCOSAMINE, A CARBOHYDRATE COMPONENT OF THE ANTIBIOTICS VANCOMYCIN AND SPORAVIRIDIN [J].
HAMADA, Y ;
KAWAI, A ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1984, 25 (47) :5413-5414