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3,28-Diacetoxylup-20(29)-ene-30-oic Acid and Its ω-Bromoalkyl Esters

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Abstract

A convenient procedure has been developed for the synthesis of 3β,28-diacetoxylup-20(29)-en-30-oic acid via oxidation of 3β,28-di-O-acetylbetulin with selenium dioxide in aqueous ethanol on heating, followed by oxidation of 3β,28-diacetoxylup-20(29)-en-30-al thus formed with sodium chlorite in tert-butyl alcohol. The alkylation of 3β,28-diacetoxylup-20(29)-en-30-oic acid with 1,3-dibrompropane and 1,5-dibromopentane in boiling acetonitrile in the presence of potassium carbonate afforded the corresponding ω-bromoalkyl esters in high yields.

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ACKNOWLEDGMENTS

The authors thank Joint Spectral and Analytical Center (Kazan Scientific Center, Russian Academy of Sciences).

Funding

The synthetic part of this study was performed under financial support by the Russian Foundation for Basic Research (project no. 19-33-90275); the spectral studies were supported by the subsidy allocated to Kazan Federal University and Kazan Scientific Center of the Russian Academy of Sciences to perform state task in the sphere of research activity.

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Authors and Affiliations

  1. Butlerov Institute of Chemistry, Kazan (Volga region) Federal University, 420008, Kazan, Russia

    D. V. Ponomaryov, L. R. Grigorʼeva, A. V. Nemtarev, O. V. Tsepaeva, V. F. Mironov & I. S. Antipin

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420008, Kazan, Russia

    A. V. Nemtarev, O. V. Tsepaeva, V. F. Mironov & I. S. Antipin

  3. Zavoisky Kazan Physical Technical Institute, Kazan Scientific Center, Russian Academy of Sciences, 420111, Kazan, Russia

    O. I. Gnezdilov

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  1. D. V. Ponomaryov
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Correspondence to A. V. Nemtarev.

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Ponomaryov, D.V., Grigorʼeva, L.R., Nemtarev, A.V. et al. 3,28-Diacetoxylup-20(29)-ene-30-oic Acid and Its ω-Bromoalkyl Esters. Russ J Org Chem 56, 626–630 (2020). https://doi.org/10.1134/S1070428020040107

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