From alpha-cedrene to crinipellin B and onward: 25 years of the alkene-arene meta-photocycloaddition reaction in natural product synthesis

Org Biomol Chem. 2006 Dec 21;4(24):4409-30. doi: 10.1039/b614011b. Epub 2006 Nov 3.

Abstract

Wender and Howbert's remarkable synthesis of alpha-cedrene in 1981 brought the attention of the synthetic community to the alkene-arene meta-photocycloaddition reaction. Here we review the natural product syntheses that have been achieved, over the last 25 years, utilising this strategic level reaction.

Publication types

  • Review

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Molecular Structure
  • Organic Chemicals / chemical synthesis*
  • Organic Chemicals / chemistry
  • Plant Oils / chemical synthesis*
  • Plant Oils / chemistry
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes

Substances

  • Biological Products
  • Organic Chemicals
  • Plant Oils
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • cedrene
  • crinipellin