A concise asymmetric route to Nuphar alkaloids. A formal synthesis of (-)-deoxynupharidine

Org Lett. 2003 Sep 18;5(19):3427-9. doi: 10.1021/ol035156t.

Abstract

[reaction: see text] A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd-TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (-)-deoxynupharidine 1 is described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Allyl Compounds / chemistry
  • Aziridines / chemistry
  • Catalysis
  • Models, Chemical
  • Nuphar*
  • Palladium / chemistry
  • Piperidines / chemical synthesis
  • Quinolizines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Allyl Compounds
  • Aziridines
  • Piperidines
  • Quinolizines
  • deoxynupharidine
  • Palladium