Applications of Lawesson's reagent in the synthesis of naturally occurring steroids and terpenoids

J Asian Nat Prod Res. 2017 Nov;19(11):1114-1123. doi: 10.1080/10286020.2017.1295229. Epub 2017 Mar 30.

Abstract

Steroids and terpenoids are among the most biologically significant classes of natural products possessing a variety of biological activities. The replacement of one or more oxygen atoms in a steroid or terpenoid molecule by a heteroatom affects the chemical properties of that particular steroid or terpenoid, and that replacement often results in alterations of its biological properties, which is sometimes valuable. One possible modification is the thionation that could have some influence on such activity. Among the various thionating reagents, Lawesson's reagent was found to be most suitable and showed versatile properties, including chemoselectivity and functional group tolerance. In this review, we present the role of Lawesson's reagent in the synthesis of thioanalogues of natural steroids and terpenoids.

Keywords: Lawesson’s reagent; steroids; terpenoids; thionation.

Publication types

  • Review

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Indicators and Reagents / chemistry*
  • Molecular Structure
  • Organothiophosphorus Compounds / chemistry*
  • Steroids / chemical synthesis*
  • Steroids / chemistry
  • Structure-Activity Relationship
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Biological Products
  • Indicators and Reagents
  • Organothiophosphorus Compounds
  • Steroids
  • Terpenes
  • 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide