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Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment

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A 1-cyano-2,3-secolupane derivative with an ethylketone fragment was synthesized from 2-hydroxyoximodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement and was used further to prepare α-bromo-substituted diastereomers. Nitrile-anionic cyclization of the ethylketone and α-bromo isomers produced cyclic derivatives with an alkenenitrile and an α,β-unsaturated ketone in ring A, respectively. The obtained compounds did not exhibit cytotoxic activity according to biological screening data.

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Acknowledgment

The work was financially supported by a grant from the Russian Science Foundation No. 21-13-00161. We thank the Center for Collective Use, PFRC, UrB, RAS, Research on Materials and Compounds, for facilitating the spectral and analytical studies and Candidate M. V. Dmitriev, Department of Organic Chemistry, Perm State Natl. Res. Univ., for performing the XSA of 4.

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Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm, 614013, Russia

    N. V. Galaiko, Yu. A. Beloglazova & V. V. Grishko

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  1. N. V. Galaiko
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  2. Yu. A. Beloglazova
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  3. V. V. Grishko
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Correspondence to V. V. Grishko.

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Ttranslated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2023, pp. 83–86.

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Galaiko, N.V., Beloglazova, Y.A. & Grishko, V.V. Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment. Chem Nat Compd 59, 94–98 (2023). https://doi.org/10.1007/s10600-023-03925-9

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  • DOI: https://doi.org/10.1007/s10600-023-03925-9

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