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Synthesis of α,ω-Diketodiesters from Betulin

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Chemistry of Natural Compounds Aims and scope

A new synthesis of 3-oxo-28-hydroxylup-20(29)-ene from the available natural triterpenoid betulin was developed. α,ω-Diketodiesters were prepared for the first time by different methods from 3-oxo-28-hydroxylup-20(29)-ene and a series of natural dicarboxylic acids. Steglich reaction conditions gave the highest yields. One of the synthesized α,ω-diketodiesters was moderately active in vitro against A-549 lung carcinoma.

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Acknowledgment

The studies were financially supported by the RFBR in the framework of Science Project No. 20-33-90200.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    V. A. Vydrina, R. R. Sayakhov, M. P. Yakovleva & G. Yu. Ishmuratov

  2. Institute of Biochemistry and Genetics, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    Z. R. Zileeva

  3. Bashkir State University, 32 Zaki Validi St, Ufa, 450076, Russia

    R. F. Talipov

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  1. V. A. Vydrina
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  2. R. R. Sayakhov
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  3. M. P. Yakovleva
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  4. Z. R. Zileeva
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  5. R. F. Talipov
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  6. G. Yu. Ishmuratov
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Correspondence to M. P. Yakovleva.

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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2021, pp. 603–607.

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Vydrina, V.A., Sayakhov, R.R., Yakovleva, M.P. et al. Synthesis of α,ω-Diketodiesters from Betulin. Chem Nat Compd 57, 706–711 (2021). https://doi.org/10.1007/s10600-021-03454-3

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  • DOI: https://doi.org/10.1007/s10600-021-03454-3

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