The chemoenzymatic synthesis of usnic acid

Bioorg Med Chem Lett. 2009 May 1;19(9):2383-5. doi: 10.1016/j.bmcl.2009.03.087. Epub 2009 Mar 26.

Abstract

Usnic acid, a highly functionalized dibenzofuran, is a polyketide secondary metabolite produced by several species of lichens. Synthesis of usnic acid from commercially available starting material was accomplished in two steps. The synthesis involves the methylation of phloracetophenone followed by oxidation with horseradish peroxidase. This work will lay the foundation for further biosynthetic studies on usnic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Chemistry, Organic / methods
  • Horseradish Peroxidase / chemistry
  • Lichens
  • Models, Chemical
  • Oxygen / chemistry

Substances

  • Anti-Infective Agents
  • Benzofurans
  • usnic acid
  • dibenzofuran
  • Horseradish Peroxidase
  • Oxygen