Unusual cyclic terpenoids with terminal pendant prenyl moieties: from occurrence to synthesis

Nat Prod Rep. 2014 Dec;31(12):1686-720. doi: 10.1039/c4np00081a.

Abstract

The paper reviews the known examples of cyclic terpenoids produced from open chain polyenic precursors by an "unusual" biosynthetic pathway, involving selective electrophilic attack on an internal double bond followed by cyclization. The resulting compounds possess cyclic backbones with pendant terminal prenyl groups. Synthetic approaches applied for the synthesis of such specifically functionalized compounds are also discussed, as well as biological activity of reported representatives.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Animals
  • Biosynthetic Pathways
  • Diterpenes / chemical synthesis
  • Diterpenes / chemistry
  • Hepatophyta / chemistry
  • Humans
  • Laurencia
  • Molecular Structure
  • Plants
  • Porifera
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology
  • Terpenes* / chemical synthesis
  • Terpenes* / chemistry
  • Terpenes* / pharmacology

Substances

  • Diterpenes
  • Sesquiterpenes
  • Terpenes