Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation

Org Lett. 2010 Feb 5;12(3):528-31. doi: 10.1021/ol902718q.

Abstract

Short and efficient access to (+)-lupinine and (+)-epiquinamide by means of an unprecedented double hydroformylation of a bis-homoallylic azide followed by a tandem catalytic hydrogenation/reductive bis-amination is reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Amination
  • Azides / chemistry
  • Catalysis
  • Hydrogenation
  • Molecular Structure
  • Quinolizines / chemical synthesis*
  • Quinolizines / chemistry
  • Sparteine / analogs & derivatives*
  • Sparteine / chemical synthesis
  • Sparteine / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Azides
  • Quinolizines
  • epiquinamide
  • Sparteine
  • lupinine