title: An efficient oxyfunctionalization of quinopimaric acid derivatives with ozone.
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.
authors.affiliation: Institute of Organic Chemistry, Ufa Research Center of Russian Academy of Sciences, 71 Prospect Oktyabrya, 450054 Ufa, Russian Federation. obf@anrb.ru
authors.forename: Oxana B
authors.initials: OB
authors.lastname: Kazakova
authors.forename: Elena V
authors.initials: EV
authors.lastname: Tretyakova
authors.forename: Irina E
authors.initials: IE
authors.lastname: Smirnova
authors.forename: Timur I
authors.initials: TI
authors.lastname: Nazyrov
authors.forename: Ol'ga S
authors.initials: OS
authors.lastname: Kukovinets
authors.forename: Genrikh A
authors.initials: GA
authors.lastname: Tolstikov
authors.forename: Kiryll Yu
authors.initials: KY
authors.lastname: Suponitskii
mesh_terms: D045784:Abietanes / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010126:Ozone / Q000737:chemistry*
chemical_list: D045784:Abietanes; C542630:dihydroquinopymaric acid; D010126:Ozone