Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type

Org Biomol Chem. 2015 Jul 28;13(28):7813-21. doi: 10.1039/c5ob01044f. Epub 2015 Jun 24.

Abstract

An esterification/Friedel-Crafts-cyclization approach permitted the first successful synthetic entry into the oxacyclododecindione subclass of the dihydroxyphenylacetic acid lactone-type natural products. This route allowed the preparation of two highly active anti-inflammatory fungal secondary metabolites 14-deoxyoxacyclododecindione and 14-deoxy-4-dechlorooxacyclododecindione as well as their 14-desmethyl analogues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Cyclization
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / chemistry
  • Molecular Structure

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Lactones
  • Macrocyclic Compounds
  • oxacyclododecindione