Asymmetric synthesis of (-)-nupharamine and (-)-(5S,8R,9S)-5-(3-furyl)-8-methyloctahydroindolizidine from beta-amino ketones and the intramolecular Mannich reaction

J Org Chem. 2006 May 26;71(11):4222-6. doi: 10.1021/jo060371j.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemical synthesis*
  • Furans / chemical synthesis*
  • Indolizines / chemical synthesis*
  • Ketones / chemistry*
  • Molecular Structure
  • Piperidines / chemical synthesis*

Substances

  • 5-(3-furyl)-8-methyloctahydroindolizidine
  • Alkaloids
  • Furans
  • Indolizines
  • Ketones
  • Piperidines
  • nupharamine