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Synthesis of 24-Noroleanolic Acid Derivatives

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Abstract

Epoxidation of 2-cyano-2,3-seco-24-nor-4(23)-ene derivatives of oleanolic acid with m-chloroper­oxy­benzoic acid, followed by treatment of the resulting epoxides with boron trifluoride–diethyl ether complex, afforded new 24-noroleanane derivatives whose structure was determined using two-dimensional NMR correlation techniques (1H–1H COSY, 1H–1H NOESY, 1H–13C HSQC, 1H–13C HMBC). Depending on the conditions, the reaction of methyl 2-cyano-2,3-seco-24-norolean-4(23)-ene-28-oate with m-chloroperoxybenzoic acid may be regioselective with the formation of 4(23)-epoxy or 12-oxo derivative, as well as allylic oxidation product of the isopropenyl moiety.

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Funding

This study was performed in the framework of state assignment (project nos. AAAA-A20-120012090023-8, AAAA-A20-120012090029-0).

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Authors and Affiliations

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

    L. M. Zakirova, E. V. Tretyakova, I. P. Baikova & O. B. Kazakova

Authors
  1. L. M. Zakirova
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  2. E. V. Tretyakova
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  3. I. P. Baikova
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  4. O. B. Kazakova
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Corresponding author

Correspondence to O. B. Kazakova.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 9, pp. 1252–1259 https://doi.org/10.31857/S0514749221090032.

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Zakirova, L.M., Tretyakova, E.V., Baikova, I.P. et al. Synthesis of 24-Noroleanolic Acid Derivatives. Russ J Org Chem 57, 1405–1411 (2021). https://doi.org/10.1134/S1070428021090037

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  • DOI: https://doi.org/10.1134/S1070428021090037

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