SYNTHESIS FROM A HEPTONOLACTONE AND EFFECT ON GLYCOSIDASES OF (1S,2R,6R,7S)-1,2,6,7-TETRAHYDROXYPYRROLIZIDINE

被引:29
作者
FAIRBANKS, AJ
FLEET, GWJ
JONES, AH
BRUCE, I
ALDAHER, S
DIBELLO, IC
WINCHESTER, B
机构
[1] DYSON PERRINS LAB,S PARKS RD,OXFORD OX1 3QY,ENGLAND
[2] INST CHILD HLTH,DEPT CLIN BIOCHEM,LONDON WC1N 1EH,ENGLAND
[3] OXFORD CTR MOLEC SCI,OXFORD OX1 3QY,ENGLAND
关键词
D O I
10.1016/0040-4020(91)80015-T
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A five step synthesis of the pseudo C2 symmetric (1S,2R,6R,7S)-1,2,6,7-tetrahydroxypyrrolizidine from 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone is reported. The effects of structure of some polyhydroxylated pyrrolizidines and pyrrolidines on inhibition of mannosidases are compared. © 1991.
引用
收藏
页码:131 / 138
页数:8
相关论文
共 20 条
[1]   CHANGE IN SPECIFICITY OF GLYCOSIDASE INHIBITION BY N-ALKYLATION OF AMINO-SUGARS [J].
ALDAHER, S ;
FLEET, G ;
NAMGOONG, SK ;
WINCHESTER, B .
BIOCHEMICAL JOURNAL, 1989, 258 (02) :613-615
[2]   IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF, AND MANNOSIDASE AND FUCOSIDASE INHIBITION BY, ALPHA-HOMOMANNOJIRMYCIN AND 6-EPI-HOMOMANNOJIRMYCIN [J].
BRUCE, I ;
FLEET, GWJ ;
DIBELLO, IC ;
WINCHESTER, B .
TETRAHEDRON LETTERS, 1989, 30 (51) :7257-7260
[3]   RETENTION AND APPARENT INVERSION DURING AZIDE DISPLACEMENT OF ALPHA-TRIFLATES OF 1,5-LACTONES [J].
BRUCE, I ;
FLEET, GWJ ;
GIRDHAR, A ;
HARALDSSON, M ;
PEACH, JM ;
WATKIN, DJ .
TETRAHEDRON, 1990, 46 (01) :19-32
[4]  
BRUCE I, UNPUB
[5]   SYNTHESIS OF THE MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND OF THE RING CONTRACTED SWAINSONINES, (1S, 2R, 7R, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE AND (1S, 2R, 7S, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE [J].
CARPENTER, NM ;
FLEET, GWJ ;
DIBELLO, IC ;
WINCHESTER, B ;
FELLOWS, LE ;
NASH, RJ .
TETRAHEDRON LETTERS, 1989, 30 (51) :7261-7264
[6]   EFFECT ON HUMAN LIVER GLYCOSIDASES AND SHORT SYNTHESES OF 1-ALPHA,2-ALPHA,6-ALPHA,7-ALPHA,7A-BETA-1,2,6,7-TETRAHYDROXYPYRROLIZIDINE FROM D-GLYCERO-D-GULO-HEPTONO-1,4-LACTONE [J].
COLLIN, WF ;
FLEET, GWJ ;
HARALDSSON, M ;
DIBELLO, IC ;
WINCHESTER, B .
CARBOHYDRATE RESEARCH, 1990, 202 :105-116
[7]   ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL [J].
COREY, EJ ;
JARDINE, PD ;
VIRGIL, S ;
YUEN, PW ;
CONNELL, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9243-9244
[8]   THE ORIGIN OF ENANTIOSELECTIVITY IN THE DIHYDROXYLATION OF OLEFINS BY OSMIUM-TETROXIDE AND CINCHONA ALKALOID DERIVATIVES [J].
COREY, EJ ;
LOTTO, GI .
TETRAHEDRON LETTERS, 1990, 31 (19) :2665-2668
[9]  
DIBELLO IC, 1989, BIOCHEM J, V259, P255
[10]  
ELIS MJ, 1985, TETRAHEDRON LETT, V26, P5397