Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives

Chemistry. 2004 Jul 5;10(13):3286-300. doi: 10.1002/chem.200305581.

Abstract

The double ring-closing metathesis reaction of nitrogen-containing tetraenes was studied. The selectivity of the fused/dumbbell-type products can be controlled by the electronic/steric effects of the substituents attached to the C[double bond]C bonds and the s-cis/s-trans conformational ratios of the substrates. This methodology has also been successfully applied to the enantioselective synthesis of four stereoisomers of lupinine and their derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkenes / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Cyclization
  • Models, Molecular
  • Nuclear Magnetic Resonance, Biomolecular
  • Sparteine / analogs & derivatives*
  • Sparteine / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Alkenes
  • Bridged Bicyclo Compounds, Heterocyclic
  • Sparteine
  • lupinine