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Synthesis of 3-Methyl Derivatives from Dihydrobetulonic Acid Methyl Ester

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Chemistry of Natural Compounds Aims and scope

A 2,3-secotriterpenoid with a methylketone was prepared from 1-hydroxyiminodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement. Functionalization of it led to the formation of 3-hydroxy- and 31-bromo-substituted derivatives; intramolecular cyclization, to the formation of a five-membered ring A with an alkene-nitrile. The synthetic products included compounds (5a and 9) with moderate cytotoxicity (IC50 25.22–46.66 μM) against MCF-7, HCT116, A549, and PC-3 cancer cells.

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Acknowledgment

The work was financially supported by Russian Science Foundation grant No. 21-13-00161. We thank the Center for Collective Use of 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 5b.

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Authors and Affiliations

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

    G. F. Krainova, Yu. A. Beloglazova & V. V. Grishko

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  1. G. F. Krainova
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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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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2023, pp. 71–76.

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Krainova, G.F., Beloglazova, Y.A. & Grishko, V.V. Synthesis of 3-Methyl Derivatives from Dihydrobetulonic Acid Methyl Ester. Chem Nat Compd 59, 80–86 (2023). https://doi.org/10.1007/s10600-023-03923-x

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