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Synthesis of Triterpenoid with an Ethylidene Fragment in the E Ring from Allobetulin

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Abstract

Allobetulin was converted to 3β-acetoxy-21β-acetyl-20β,28-epoxy-18α,19β-ursane, followed by reduction of the acetyl fragment and acid-catalyzed dehydration product. The structure of the obtained triterpenoid containing a trans-ethylidene substituent on the E ring was determined using two-dimensional 1H–1H COSY, 1H–1H NOESY, 1H–13C HSQC, 1H–13C HMBC correlation techniques.

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ACKNOWLEDGMENTS

The NMR and mass spectra were recorded at the Chemistry joint center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences) and Agidel regional joint center (Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 19-33-60083) and in the framework of state assignment no. AAAAA20-120012090029-0.

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Authors and Affiliations

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

    Z. I. Galimova, M. S. Babaev, A. N. Lobov & O. B. Kazakova

Authors
  1. Z. I. Galimova
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  2. M. S. Babaev
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  3. A. N. Lobov
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  4. O. B. Kazakova
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Corresponding author

Correspondence to O. B. Kazakova.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 6, pp. 895–900 https://doi.org/10.31857/S0514749221060148.

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Galimova, Z.I., Babaev, M.S., Lobov, A.N. et al. Synthesis of Triterpenoid with an Ethylidene Fragment in the E Ring from Allobetulin. Russ J Org Chem 57, 1012–1016 (2021). https://doi.org/10.1134/S1070428021060208

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