First diastereoselective chiral synthesis of (-)-securinine

Org Lett. 2004 Jan 8;6(1):87-9. doi: 10.1021/ol0361251.

Abstract

[reaction: see text] A diastereoselective total synthesis of securinine in optically pure form was achieved by employing ring-closing metathesis of the corresponding dienyne compound as a key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Azepines / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, Bridged-Ring
  • Lactones / chemical synthesis*
  • Models, Chemical
  • Molecular Structure
  • Pipecolic Acids / chemistry
  • Piperidines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Azepines
  • Heterocyclic Compounds, 4 or More Rings
  • Heterocyclic Compounds, Bridged-Ring
  • Lactones
  • Pipecolic Acids
  • Piperidines
  • securinine