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Synthesis of Cyclopropylmethyl Esters of Maleopimaric Acid and Diketocage Derivatives of Quinopimaric Acid by a Catalytic Reaction of the Corresponding Allyl Esters with Diazomethane

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Abstract

A Pd(acac)2-catalyzed reaction of allyl esters of maleopimaric and diketocage quinopimaric acid derivative with diazomethane was studied for the first time with the aim to obtain cyclopropylmethyl derivatives of the pimaric acid series as potential pharmacologically active compounds. It was shown that the reaction proceeds under mild conditions and provides the desired cyclopropylmethyl derivatives in yields of 84–98%.

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ACKNOWLEDGMENTS

The IR, 1H and 13C NMR, and mass spectra performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry UFRS RAS.

Funding

The work was performed according to the State order no. AAAA-A17-117011910025-6 (Synthesis of Biologically Active Heterocyclic and Terpenoid Compounds).

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Correspondence to G. F. Vafina.

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Vafina, G.F., Khanova, M.D. Synthesis of Cyclopropylmethyl Esters of Maleopimaric Acid and Diketocage Derivatives of Quinopimaric Acid by a Catalytic Reaction of the Corresponding Allyl Esters with Diazomethane. Russ J Org Chem 56, 346–349 (2020). https://doi.org/10.1134/S1070428020020293

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  • DOI: https://doi.org/10.1134/S1070428020020293

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