- SYNTHESIS OF THE α-MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL FROM MANNOSE
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4-azido-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside is a key intermediate in the syntheses of the α-mannosidase inhibitors, swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol, and of the α-galactosidase inhibitor 1,4-dideoxy-1,4-imino-D-lyxitol, from mannose.
- Bashyal, Bharat P.,Fleet, George W. J.,Gough, Max J.,Smith, Paul W.
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p. 3083 - 3094
(2007/10/02)
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- ENANTIOSPECIFIC SYNTHESIS OF SWAINSONINE, (1S, 2R, 8R, 8aR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE, FROM D-MANNOSE
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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.
- Fleet, G. W. J.,Gough, M. J.,Smith, P. W.
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p. 1853 - 1856
(2007/10/02)
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