ENANTIOSPECIFIC SYNTHESIS OF SWAINSONINE, (1S, 2R, 8R, 8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE, FROM D-MANNOSE

ENANTIOSPECIFIC SYNTHESIS OF SWAINSONINE, (1S, 2R, 8R, 8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE, FROM D-MANNOSE

An enantiospecific synthesis of swainsonine from D-mannose is described; the heterocyclic rings of swainsonine are constructed by two intramolecular reductive aminations caused by the catalytic hydrogenation of an azidoaldehyde with 5 equivalents of hydrogen. © 1984.

Bibliographic Details
Main Authors:	Fleet, G, Gough, M, Smith, P
Format:	Journal article
Language:	English
Published:	1984

Similar Items

SYNTHESIS OF THE ALPHA-MANNOSIDASE INHIBITORS SWAINSONINE [(1S, 2R, 8R, 8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE] AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL FROM MANNOSE
by: Bashyal, B, et al.
Published: (1987)

(6S)-Methyl-L-swainsonine [(1R, 2S, 6S, 8S, 8aS)-6-methyloctahydroindolizine-1,2,8-triol]
by: Hakansson, A, et al.
Published: (2007)

3,6-DIDEOXY-3,6-IMINO-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE AS A DIVERGENT INTERMEDIATE FOR THE SYNTHESIS OF HYDROXYLATED PYRROLIDINES - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-L-GULITOL, 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL, 2S,3S,4R-3,4-DIHYDROXYPROLINE AND (1S,2R,8S,8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE [8-EPI-SWAINSONINE] - X-RAY CRYSTAL-STRUCTURE OF (1S,2R,8S,8AR)-1,2,8-TRIHYDROXY-5-OXO-OCTAHYDROINDOLIZINE
by: Austin, G, et al.
Published: (1987)

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
by: Carpenter, N, et al.
Published: (1989)

(±)-(4aR,5R,8S,8aR)-8-(tert-Butyldimethylsilyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione
by: Fernanda G. Finelli, et al.
Published: (2013-03-01)

X-RAY CRYSTAL-STRUCTURE OF THE HYDROCHLORIDE OF 6-EPICASTANOSPERMINE [(1S,6R,7R,8R,8AR)-1,6,7,8-TETRAHYDROXY-OCTAHYDROINDOLIZINE]
by: Nash, R, et al.
Published: (1990)

Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol.
by: Araújo, N, et al.
Published: (2012)

(4aS,5R,7R,8S,8aR)-8-(1,3-Dioxolan-2-yl)-7,8-dimethyl-5-(1-methylethenyl)perhydronaphthalen-2-one
by: Maxime A. Siegler, et al.
Published: (2008-01-01)

(1R,5S,8R)-1,8-dihydroxy-6-oxa-3-azabicyclo[3.2.1]octan-2-one
by: Punzo, F, et al.
Published: (2004)

(4aR,8aR)-2,3-Diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline
by: Heng-Yun Ye, et al.
Published: (2008-02-01)

Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2r,5r-dihydroxymethyl-3r,4r-dihydroxypyrrolidine from D-glucose
by: Fleet, G, et al.
Published: (1985)

ENANTIOSPECIFIC SYNTHESES OF DEOXYMANNOJIRIMYCIN, FAGOMINE AND 2R,5R-DIHYDROXYMETHYL-3R,4R-DIHYDROXYPYRROLIDINE FROM D-GLUCOSE
by: Fleet, G, et al.
Published: (1985)

rac-(4aR,8aR)-2,3-Diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline
by: Fang Chen, et al.
Published: (2008-07-01)

3-(4-Chlorophenyl)-1-[(2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]prop-2-en-1-one
by: Mohamed Tebbaa, et al.
Published: (2011-06-01)

ENANTIOSPECIFIC SYNTHESES OF INTERMEDIATES IN THE TOTAL SYNTHESIS OF PSEUDOMONIC ACIDS
by: Fleet, G, et al.
Published: (1982)

N-[(1aR,5aR,8R,9aR)-1,1-Dichloro-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-yl]acetamide
by: Ahmed Benharref, et al.
Published: (2017-04-01)

Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxymethyl- 5-methyloctahydroindolizine-1,2- diol hydrobromide]
by: Thompson, A, et al.
Published: (2009)

Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine
by: Hakansson, A, et al.
Published: (2008)

Regiospecific and Enantiospecific Ring Opening of Methyl (+)-(1'R, 2R)- and (-)-(1'R, 2S)-1-(2-phenylethanol) Aziridine-2-carboxylates
by: W. F. Reynolds, et al.
Published: (2000-08-01)

(1R,2R,3S,6aS,7R,8R,9S,12aS)-1,2,3,7,8,9-Hexahydroxy-perhydro-dipyrido[1,2-a:1',2'-d]pyrazine-6,12-dione.
by: Jenkinson, S, et al.
Published: (2010)

ENANTIOSPECIFIC TOTAL SYNTHESIS OF PSEUDOMONIC ACIDS FROM ARABINOSE
by: Fleet, G, et al.
Published: (1983)

Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxymethyl-5-methyloctahydroindolizine-1,2-diol hydrobromide]
by: Amber L. Thompson, et al.
Published: (2009-11-01)

AN ENTRY TO CHIRAL CYCLOHEXENES FROM CARBOHYDRATES - A SHORT, EFFICIENT, AND ENANTIOSPECIFIC SYNTHESIS OF (-)-SHIKIMIC ACID FROM D-MANNOSE
by: Fleet, G, et al.
Published: (1983)

Synthesis and crystal structure of (2S,4aR,8aR)-6-oxo-2,4a,6,8a-tetrahydropyrano[3,2-b]pyran-2-carboxamide
by: John Greene, et al.
Published: (2020-05-01)

(1R,2R,3S,6aS,7R,8R,9S,12aS)-1,2,3,7,8,9-Hexahydroxyperhydrodipyrido[1,2-a:1&#8242;,2&#8242;-d]pyrazine-6,12-dione
by: S. F. Jenkinson, et al.
Published: (2010-04-01)

(4aR*,8aS*)-2,3-Diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline
by: W. Chen, et al.
Published: (2012-07-01)

STRUCTURE ACTIVITY RELATIONSHIP OF SWAINSONINE - INHIBITION OF HUMAN ALPHA-MANNOSIDASES BY SWAINSONINE ANALOGS
by: Dibello, I, et al.
Published: (1989)

Crystal structure of (3aR*,6aR*,9aR*,9bS*)-decahydro-8,8-dimethyl-6,9-dioxo-9a-methoxycarbonylazuleno[4,5-c]furan-1(3H)-one, (CH3)2C10H8O2(COOCH3)2
by: Peters K., et al.
Published: (1999-09-01)

Ethyl (4aR*,7S*,8S*,8aS*)-1-oxo-7-phenyl-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate
by: Xiu Qing Jiang, et al.
Published: (2010-06-01)

SYNTHESIS FROM D-GLUCOSE OF ALEXINE [(1R,2R,3R,7S,8S)-3-HYDROXYMETHYL-1,2,7-TRIHYDROXYPYRROLIZIDINE], 3-EPIALEXINE AND 7-EPIALEXINE
by: Fleet, G, et al.
Published: (1988)

THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
by: Bashyal, B, et al.
Published: (1987)

ENANTIOSPECIFIC SYNTHESIS OF SHIKIMIC ACID FROM D-MANNOSE - FORMATION OF A CHIRAL CYCLOHEXENE BY INTRAMOLECULAR OLEFINATION OF A CARBOHYDRATE-DERIVED INTERMEDIATE
by: Fleet, G, et al.
Published: (1984)

Crystal structure of (1'R*,3R*,3aR*,4S*,8aR*)-dimethyl 1',3-epoxydecahydro- 3,5-(2'-oxapropanylidene)-8-oxo-azulene-3a,4-dicarboxylate, C12H12O3(COOCH3)2
by: Peters K., et al.
Published: (1999-03-01)

Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxy-meth-yl-5-methyl-octa-hydro-indolizine-1,2-diol hydro-bromide].
by: Thompson, A, et al.
Published: (2009)

ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2S,4S,5S-DIHYDROXYPIPECOLIC ACID, AND BULGECININE FROM DEUTERIUM-GLUCURONOLACTONE
by: Bashyal, B, et al.
Published: (1986)

Crystal structure of (3aR*,4S*,8S*,8aR*)-dimethyl decahydro-8-hydroxy(2'-oxapropane-diyliden)azulene-3a,4-dicarboxylate, C16H20O6
by: Peters K., et al.
Published: (1998-04-01)

Diaqua[(1R,2S,4R,8R,9S,11R)-2,9-dimethyl-1,4,8,11-tetraazacyclotetradecane]nickel(II) dichloride dihydrate
by: James Alan Townsend, et al.
Published: (2012-08-01)

Crystal structure of (3aR*,6aR*,9aR*,9bR*)-spiro[(1’,3’-dioxolane)-2’,6-(decahydro-8,8-dimethyl- 9-oxoazuleno[4,5-c]furan-1(3H)-one)], (CH3)2C14H16O5
by: Peters K., et al.
Published: (1999-09-01)

(3aR,8aS,9S,9aR)-9-Hydroxyperhydrofuro[3,2-f]indolizin-6-one
by: &#317;ubom&#237;r &#352;vorc, et al.
Published: (2009-08-01)

(2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hydroxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octahydro-1H-pentaleno[1,6-bc]oxepine-4-carboxylate
by: Goverdhan Mehta, et al.
Published: (2012-12-01)