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

Article abstract of DOI:10.1016/S0040-4039(01)90059-0

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.