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Published on: June 20, 2014
An efficient oxyfunctionalization of quinopimaric acid derivatives with ozone
Oxana B Kazakova1, Elena V Tretyakova, Irina E Smirnova
1Institute of Organic Chemistry, Ufa Research Center of Russian Academy of Sciences, 71 Prospect Oktyabrya, 450054 Ufa, Russian Federation. obf@anrb.ru
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.
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