Total synthesis of (+/-)-syn-copalol

Biosci Biotechnol Biochem. 2002 Nov;66(11):2504-10. doi: 10.1271/bbb.66.2504.

Abstract

The labdane diterpene derivative, syn-copalol [(+)-5] is the alcohol part of syn-copalyl diphosphate [(+)-4]. In this paper, racemic (+/-)-5 was synthesized from a known racemic lactone in 8 steps. The current and our previous syntheses provide all four copalol derivatives [(+)-3, (-)-3 and (+/-)-5] which are required for the biosynthetic study of polycyclic diterpenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / metabolism
  • Lactones / chemistry
  • Organophosphates / chemistry*
  • Stereoisomerism

Substances

  • Diterpenes
  • Lactones
  • Organophosphates
  • copalyl diphosphate
  • labdane
  • copalol