1ST SYNTHESIS OF (1R,2R,3S,9S,9AR)-1,2,3,9-TETRAHYDROXY-QUINOLIZIDINE, A NOVEL ISOSTERIC HOMOLOG OF THE GLUCOSIDASE INHIBITOR CASTANOSPERMINE

被引：37

作者：

GRADNIG, G

BERGER, A

GRASSBERGER, V

STUTZ, AE

LEGLER, G

机构：

[1] GRAZ TECH UNIV,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

[2] UNIV COLOGNE,INST BIOCHEM,W-5000 COLOGNE,GERMANY

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 37期

关键词：

CASTANOSPERMINE; GLUCOSIDASE INHIBITOR; HOMOLOG; SYNTHESIS;

D O I：

10.1016/S0040-4039(00)93488-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta-L-ido-hexodialdodifuranose, prepared from D-glucofuranurono-6,3-lactone in four highly efficient steps, with the Grignard reagent generated from 2-(2-bromoethyl)-1,3-dioxolane gave a protected nonodialdose which was transformed into a tetrahydroxyquinolizidine essentially isosteric and homologous with castanospermine.

引用

页码：4889 / 4892

页数：4

共 20 条

[1] ENANTIOSPECIFIC SYNTHESIS OF POLYHYDROXYLATED INDOLIZIDINES RELATED TO CASTANOSPERMINE .3. SYNTHESIS OF 1-DEOXY-6-EPICASTANOSPERMINE AND 1-DEOXY-6,8A-DIEPICASTANOSPERMINE
AAMLID, KH
HOUGH, L
RICHARDSON, AC
[J]. CARBOHYDRATE RESEARCH, 1990, 202 : 117 - 129
[2] BUCHI G, 1969, J ORG CHEM, V34, P1122
[3] SIMPLE SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL(1-DEOXYNOJIRIMYCIN) AND 1,6-DIDEOXY-1,6-IMINO-D-GLUCITOL FROM D-GLUCOFURANURONO-6,3-LACTONE
DAX, K
GAIGG, B
GRASSBERGER, V
KOLBLINGER, B
STUTZ, AE
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (04) : 479 - 499
[4] DAX K, 1991, IN PRESS CARBOHYDR R
[5] EKHART C, UNPUB
[6] SYNTHESIS OF THE ENANTIOMERS OF 6-EPICASTANOSPERMINE AND 1,6-DIEPICASTANOSPERMINE FROM D-GULONOLACTONE AND L-GULONOLACTONE
FLEET, GWJ
RAMSDEN, NG
NASH, RJ
FELLOWS, LE
JACOB, GS
MOLYNEUX, RJ
DIBELLO, IC
WINCHESTER, B
[J]. CARBOHYDRATE RESEARCH, 1990, 205 : 269 - 282
[7] SYNTHESIS OF 6-EPICASTANOSPERMINE AND 1,6-DIEPICASTANOSPERMINE FROM L-GULONOLACTONE AND SYNTHESIS OF L-6-EPICASTANOSPERMINE AND L-1,6-DIEPICASTANOSPERMINE FROM D-GULONOLACTONE
FLEET, GWJ
RAMSDEN, NG
MOLYNEUX, RJ
JACOB, GS
[J]. TETRAHEDRON LETTERS, 1988, 29 (29) : 3603 - 3606
[8] GRADNIG G, UNPUB
[9] INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE
GRUTERS, RA
NEEFJES, JJ
TERSMETTE, M
DEGOEDE, REY
TULP, A
HUISMAN, HG
MIEDEMA, F
PLOEGH, HL
[J]. NATURE, 1987, 330 (6143) : 74 - 77
[10] ENANTIOSPECIFIC SYNTHESIS OF 1-DEOXY-CASTANOSPERMINE, (6S, 7R, 8R, 8AR)-TRIHYDROXYINDOLIZIDINE, FROM D-GLUCOSE
HENDRY, D
HOUGH, L
RICHARDSON, AC
[J]. TETRAHEDRON LETTERS, 1987, 28 (39) : 4597 - 4600

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