TOTAL SYNTHESIS OF SIASTATIN-B AND ITS ENANTIOMER USING CARBOHYDRATE AS A CHIRAL EDUCT

被引:20
作者
NISHIMURA, Y
WANG, WM
KUDO, T
机构
[1] Institute of Microbial Chemistry, Shinagawa-ku, Tokyo 141
关键词
D O I
10.1246/bcsj.65.978
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective synthesis of siastatin B, an inhibitor of neuraminidase and its antipode from D-ribono-gamma-lactone has stereospecifically been achieved. The total synthesis elucidated the absolute configuration of siastatin B as (3S,4S,5R,6R)-6-acetamido-4,5-dihydroxy-3-piperidinecarboxylic acid.
引用
收藏
页码:978 / 986
页数:9
相关论文
共 66 条
[1]  
ANDERSON RC, 1978, TETRAHEDRON LETT, P3233
[2]  
BHAT KL, 1985, HETEROCYCLES, V23, P691
[3]  
BLACK DSC, 1972, TETRAHEDRON LETT, P1331
[4]   TOTAL SYNTHESIS OF SLOW REACTING SUBSTANCES (SRSS) - 6-EPI-LEUKOTRIENE-C AND 6-EPI-LEUKOTRIENE-D [J].
COREY, EJ ;
GOTO, G .
TETRAHEDRON LETTERS, 1980, 21 (36) :3463-3466
[5]  
Corfield A.P., 1981, PERSPECTIVES INHERIT, V4, P3
[6]  
CORFIELD AP, 1982, SIALIC ACIDS CHEM ME, P5
[7]   ISOLATION AND STRUCTURE OF AN UNUSUAL CYCLIC AMINO ALDITOL FROM A LEGUME [J].
FELLOWS, LE ;
BELL, EA ;
LYNN, DG ;
PILKIEWICZ, F ;
MIURA, I ;
NAKANISHI, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :977-978
[8]   DESIGN SYNTHESIS AND PRELIMINARY EVALUATION OF A POTENT ALPHA-MANNOSIDASE INHIBITOR - 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL [J].
FLEET, GWJ ;
SMITH, PW ;
EVANS, SV ;
FELLOWS, LE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1240-1241
[9]   UNIQUE METHODOLOGY FOR CONJUGATE REDUCTION AND REDUCTIVE ALKYLATION OF ALPHA,BETA-UNSATURATED CARBOXYLIC ESTERS [J].
GANEM, B ;
FORTUNATO, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (19) :2846-2848
[10]   BRANCHED-CHAIN SUGARS .10. SYNTHESIS OF BRANCHED-CHAIN AMINO-SUGARS [J].
GUNNER, SW ;
KING, RD ;
OVEREND, WG ;
WILLIAMS, NR .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (14) :1954-&