An efficient asymmetric synthesis of (-)-lupinine

Chem Commun (Camb). 2014 Aug 7;50(61):8309-11. doi: 10.1039/c4cc02135e.

Abstract

The asymmetric synthesis of (-)-lupinine was achieved in 8 steps, 15% overall yield and >99 : 1 dr from commercially available starting materials. The strategy used for the construction of the quinolizidine scaffold involved reaction of an enantiopure tertiary dibenzylamine via two sequential ring-closures which both occurred with concomitant N-debenzylation.

MeSH terms

  • Alkylation
  • Cyclization
  • Quinolizidines / chemistry
  • Sparteine / analogs & derivatives*
  • Sparteine / chemical synthesis
  • Sparteine / chemistry
  • Stereoisomerism

Substances

  • Quinolizidines
  • Sparteine
  • lupinine