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Oxidation of Cage Derivatives of Quinopimaric Acid

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Abstract

The oxidation of cage compounds derived from quinopimaric acid, namely γ-diketone, oxa-“bird cage,” 18-chloro-15-oxa-“bird cage,” and 16-sulfanyl-15-oxa-“bird cage,” was studied using a number of oxidating agents, including sodium percarbonate in trifluoroacetic acid at 0°C, 36% hydrogen peroxide in acetone at room temperature, and tert-butyl hydroperoxide in the presence of MoCl5 in boiling benzene. It was shown for the first time that the oxidation of diterpene oxa-“bird cages” led to the formation of mixtures of keto lactones (Baeyer–Villiger oxidation products), in which 7,10-dioxo-6-oxaheptacyclo[11.8.0.03,8.04,12.05,11.09,13.016,21]heneicosane was the major component.

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ACKNOWLEDGMENTS

The NMR spectra were recorded using the equipment of the Chemistry joint center, Ufa Institute of Chemistry, Russian Academy of Sciences.

Funding

This study was performed in the framework of state assignment no. 1021062311395-6-1.4.1 (Synthesis of Bio­logically Active Compounds Based on Natural Compounds. Design of Environmentally Benign Materials and Tech­nologies).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    G. F. Vafina & A. N. Lobov

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  1. G. F. Vafina
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  2. A. N. Lobov
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Correspondence to G. F. Vafina.

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Dedicated to Full Member of the Russian Academy of Sciences G.A. Tolstikov on his 90th anniversary

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Vafina, G.F., Lobov, A.N. Oxidation of Cage Derivatives of Quinopimaric Acid. Russ J Org Chem 60, 423–429 (2024). https://doi.org/10.1134/S1070428024030084

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