Asymmetric synthesis of (R)-antofine and (R)-cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde

J Org Chem. 2010 Oct 15;75(20):7018-21. doi: 10.1021/jo101510x.

Abstract

Naturally occurring phenanthroindolizidine alkaloids (R)-antofine and phenanthroquinolizidine alkaloids (R)-cryptopleurine have been synthesized in high optical purity via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde. Both enantiopure forms of proline are commercially available, and thus, in principle, both isomers of antofine and cryptopleurine can be accessed with the new method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Catalysis
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Phenanthrolines / chemical synthesis*
  • Phenanthrolines / chemistry
  • Proline / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Alkaloids
  • Indoles
  • Phenanthrolines
  • antofine
  • cryptopleurine
  • Proline