An efficient oxyfunctionalization of quinopimaric acid derivatives with ozone

Nat Prod Commun. 2013 Mar;8(3):293-6.

Abstract

An access to oxyfunctionalized quinopimaric acid derivatives is reported. The ozonolysis of methyl dihydroquinopimarate occurs through 1,2-cycloaddition of ozone to the bridging double bond followed by intermolecular rearrangements and formation of nontrivial 4beta-hydroxy-4alpha,14alpha-epoxy-13(15)-ene derivative 2. The oxidation of methyl furfurilydene dihydroquinopimarate with ozone led to anhydride 5 and unexpected carboxymethyl substituted cyclopentane lactone 6. The structure of compound 6 was confirmed by X-Ray analysis of its methyl ester.

MeSH terms

  • Abietanes / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Ozone / chemistry*

Substances

  • Abietanes
  • dihydroquinopymaric acid
  • Ozone