Novel domino reactions for diterpene synthesis

J Org Chem. 2004 Dec 10;69(25):8935-7. doi: 10.1021/jo049616n.

Abstract

New types of concerted domino acylation-cycloalkylation/alkylation-cycloacylation reactions have been described. These processes promoted by methanesulfonic acid-phosphorus pentoxide and concentrated H(2)SO(4), respectively, provide efficient, elegant, and expeditious routes for biologically active naturally occurring diterpenoids, namely (+/-)-ferruginol (1), (+/-)-nimbidiol (2), (+/-)-nimbiol (3), (+/-)-totarol (4), and ar-abietatriene (5).

MeSH terms

  • Abietanes
  • Acylation
  • Alkylation
  • Cyclization
  • Cyclopropanes / chemical synthesis*
  • Diterpenes / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism

Substances

  • 1-phenylcyclopropene
  • Abietanes
  • Cyclopropanes
  • Diterpenes
  • ar-abietatriene
  • ferruginol
  • nimbidiol
  • totarol
  • nimbiol