An Efficient Oxyfunctionalization of Quinopimaric Acid Derivatives with Ozone
2013 ◽
Vol 8
(3)
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pp. 1934578X1300800
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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 4β-hydroxy-4α,14α-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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1982 ◽
pp. 594
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1984 ◽
pp. 480-482
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2018 ◽
Vol 18
(5)
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pp. 3249-3268
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