title: Asymmetric synthesis of (-)-nupharamine and (-)-(5S,8R,9S)-5-(3-furyl)-8-methyloctahydroindolizidine from beta-amino ketones and the intramolecular Mannich reaction.
abstract: The asymmetric synthesis of the 2,3,6-trisubstituted piperidine core of the antitumor Nuphar alkaloids was readily achieved by using the intramolecular Mannich reaction and a sulfinimine-derived beta-amino ketone.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
authors.forename: Franklin A
authors.initials: FA
authors.lastname: Davis
authors.forename: Manikandan
authors.initials: M
authors.lastname: Santhanaraman
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*
chemical_list: C520123:5-(3-furyl)-8-methyloctahydroindolizidine; D000470:Alkaloids; D005663:Furans; D007212:Indolizines; D007659:Ketones; D010880:Piperidines; C520122:nupharamine