Asymmetric synthesis of (-)-nupharamine and (-)-(5S,8R,9S)-5-(3-furyl)-8-methyloctahydroindolizidine from beta-amino ketones and the intramolecular Mannich reaction.
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.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Santhanaraman
Manikandan
M
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*
C520123:5-(3-furyl)-8-methyloctahydroindolizidine; D000470:Alkaloids; D005663:Furans; D007212:Indolizines; D007659:Ketones; D010880:Piperidines; C520122:nupharamine