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Ozonolytic Transformations of (S)-(–)-Limonene and Abietic Acid in the Presence of Pyridine

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Controlled ozonolysis of (S)-(–)-limonene in the presence of Py gave 4-methyl-3-(3-oxobutyl)pent-4-enal or 4-methyl-3-(3-oxobutyl)pent-4-enoic acid depending on the solvent (CH2Cl2 or MeOH). Exhaustive ozonolysis produced 3-acetyl-6-oxoheptanoic acid. Ozonolysis of abietic acid in CH2Cl2 in the presence of Py formed stable epoxytrioxolaneabietic acid; in MeOH–Py, the epoxyketoaldehyde corresponding to cleavage of the C13–C14 bond.

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Acknowledgment

The work was financially supported by RAS program “Basic Principles of Chemistry” on topic No. 8 “Chemo-, regio-, and stereoselective transformations of terpenoids, steroids, and lipids for synthesizing low-molecular-mass bioregulators” (State Reg. No. AAAA-A17-117011910023-2, 2017).

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Authors and Affiliations

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

    Yu. V. Myasoedova, L. R. Garifullina, E. R. Nurieva, A. A. Kravchenko & G. Yu. Ishmuratov

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  1. Yu. V. Myasoedova
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  2. L. R. Garifullina
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  3. E. R. Nurieva
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  4. A. A. Kravchenko
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  5. G. Yu. Ishmuratov
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Correspondence to Yu. V. Myasoedova.

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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2019, pp. 406–408.

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Myasoedova, Y.V., Garifullina, L.R., Nurieva, E.R. et al. Ozonolytic Transformations of (S)-(–)-Limonene and Abietic Acid in the Presence of Pyridine. Chem Nat Compd 55, 474–477 (2019). https://doi.org/10.1007/s10600-019-02718-3

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  • DOI: https://doi.org/10.1007/s10600-019-02718-3

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