Total enantioselective synthesis of (-)-cytisine

Org Lett. 2004 Feb 19;6(4):493-6. doi: 10.1021/ol0361507.

Abstract

[reaction: see text] The first total enantiosynthesis of the biologically active alkaloid (-)-cytisine is reported, featuring a ruthenium-catalyzed RCM reaction as the key step. The approach relies on readily available cis-piperidine-3,5-dimethanol monoacetate as the chiral building block, and it is suited for achieving the target compound in both enantiomeric forms.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Azocines / chemical synthesis*
  • Catalysis
  • Fabaceae / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Quinolizines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Azocines
  • Indicators and Reagents
  • Quinolizines
  • cytisine