Enantioselective total synthesis of valeriananoids A-C

Org Lett. 2004 Jul 8;6(14):2337-9. doi: 10.1021/ol049341y.

Abstract

[reaction: see text] The first enantioselective total synthesis of valeriananoids A-C (-)-1-3 is reported starting from the readily available monoterpene (R)-carvone, employing a tandem intermolecular Michael addition-intramolecular Michael addition-alkylation sequence and an electron-transfer-mediated 6-endo-trig cyclization as key steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Cyclization
  • Cyclohexane Monoterpenes
  • Indicators and Reagents
  • Molecular Structure
  • Monoterpenes
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Stereoisomerism
  • Terpenes / chemistry*
  • Valerian / chemistry

Substances

  • Cyclohexane Monoterpenes
  • Indicators and Reagents
  • Monoterpenes
  • Sesquiterpenes
  • Terpenes
  • valeriananoid A
  • valeriananoid B
  • valeriananoid C
  • carvone