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Chemoselective oxidation of oleanolic acid derivatives with ozone

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Chemistry of Natural Compounds Aims and scope

A method for preparing methyl esters of 12-oxoolean-28-oic and 3,12-dioxoolean-28-oic acids via ozonolysis of oleanolic acid methyl ester in CH2Cl2 at –60°C was proposed. It was found that oxidation of 2-cyano3,4-seco-4(23)-oleanenoic acid was chemoselective depending on the amount of ozone used.

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Acknowledgment

The work was supported financially partly by the RFBR (Project No. 09-03-00831). N. I. Medvedeva is grateful to the Visegrad Fund for financial support (Grant No. 977085).

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, prosp. Oktyabrya, 71, Russia

    O. B. Kazakova, N. I. Medvedeva, O. S. Kukovinets, G. A. Tolstikov & E. F. Khusnutdinova

  2. Chair and Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Poznan, Poland

    L. Zaprutko & B. Bednarczyk-Cwynar

  3. Department of Bioorganic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Poznan, Poland

    Z. Paryzek

Authors
  1. O. B. Kazakova
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  2. N. I. Medvedeva
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  3. O. S. Kukovinets
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  4. G. A. Tolstikov
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  5. E. F. Khusnutdinova
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  6. L. Zaprutko
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  7. B. Bednarczyk-Cwynar
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  8. Z. Paryzek
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Corresponding author

Correspondence to O. B. Kazakova.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 336–338, May–June, 2010.

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Kazakova, O.B., Medvedeva, N.I., Kukovinets, O.S. et al. Chemoselective oxidation of oleanolic acid derivatives with ozone. Chem Nat Compd 46, 397–399 (2010). https://doi.org/10.1007/s10600-010-9627-0

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  • DOI: https://doi.org/10.1007/s10600-010-9627-0

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