Oxidation Reactions of Cage Derivatives of Quinopimaric Acid

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Abstract

Oxidation reactions of cage derivatives of quinopimaric acid – γ-diketone, oxa-“bird cage”, 18-chloro-15-oxa-“bird cage”, and 16-sulfanyl-15-oxa-“bird cage” were studied using a number of oxidizing agents: sodium percarbonate in trifluoroacetic acid at 0°C; 36% hydrogen peroxide in acetone at room temperature; tertiary butyl hydroperoxide in the presence of MoCl5 at boiling in benzene. It has been shown for the first time that the oxidation reactions of diterpene oxa-“bird cages” lead to the formation of a mixture of ketolactones (Bayer–Villiger reaction products) with a predominance of mainly 7,10-dioxo-6-oxahepta-cyclo[11.8.0.03,8.04,12.05,11.09,13.016,21]henicosan.

About the authors

G. F. Vafina

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences (UFRC RAS)

Email: vafina@anrb.ru; ms.vafina@mail.ru
prosp. Oktabrya, 71, Ufa, 450054 Russia

A. N. Lobov

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences (UFRC RAS)

prosp. Oktabrya, 71, Ufa, 450054 Russia

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