Diastereoselective formal synthesis of a monoterpene alkaloid, (-)-incarvilline

J Org Chem. 2007 Aug 17;72(17):6541-7. doi: 10.1021/jo0709091. Epub 2007 Jul 21.

Abstract

Diastereoselective formal synthesis of a monoterpene alkaloid, (-)-incarvilline, the key intermediate for the synthesis of (-)-incarvillateine, was achieved by using an intramolecular Pauson-Khand reaction of (S)-N-[(E)-2-butenyl]-N-(3-butynyl-2-methoxymethoxy)-p-toluenesulfonamide as a key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Monoterpenes / chemical synthesis*
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism

Substances

  • Alkaloids
  • Monoterpenes
  • incarvillateine