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

An efficient oxyfunctionalization of quinopimaric acid derivatives with ozone.

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1
Institute 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.

PMID:
23678794
[Indexed for MEDLINE]
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