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Synthesis and Properties of Methyl 3,4-Epoxy-3,11-dioxo-3,4seco-18β-olean-12-ene-30-carboxylate in a New Reaction of Organoaluminium Compounds

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Abstract

An effective reagent (performic acid) was proposed for the Bayer–Villiger oxidation of glycyrrhetic acid methyl ester to the corresponding oxepan-2-one. The low-temperature (–70°C) reduction of the latter with excess (5 equiv) diisobutylaluminium hydride in CH2Cl2 resulted in the isolation of 3,4-seco-18β-oleane-4(23),9(11),12-triene-3,30-diol as the main product, while the expected (R)-3,4-epoxy-3-isobutoxy-3,4-seco-18β-oleane-11,12-dien-30-ol was the minor product.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Ufa Research Center, Russian Academy of Sciences.

Funding

The work was financially supported by the “Fundamentals of Chemistry” Program of the Russian Academy of Sciences, topic no. 8 “Chemo-, Regio-, and Stereoselective Transformations of Terpenoids, Steroids, and Lipids in the Directed Synthesis of Low-Molecular-Weight Bioregulators” (State Registration no. AAAA-A17-117011910023-2, 2017).

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Authors and Affiliations

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

    V. A. Vydrina, A. A. Kravchenko, R. R. Sayakhov, A. G. Tolstikov & G. Yu. Ishmuratov

  2. Institute of Petroleum, Chemistry and Nanotechnology, Kazan National Research Technological University, 420015, Kazan, Russia

    D. A. Sataraev

Authors
  1. V. A. Vydrina
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  2. A. A. Kravchenko
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  3. D. A. Sataraev
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  4. R. R. Sayakhov
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  5. A. G. Tolstikov
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  6. G. Yu. Ishmuratov
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Correspondence to G. Yu. Ishmuratov.

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Vydrina, V.A., Kravchenko, A.A., Sataraev, D.A. et al. Synthesis and Properties of Methyl 3,4-Epoxy-3,11-dioxo-3,4seco-18β-olean-12-ene-30-carboxylate in a New Reaction of Organoaluminium Compounds. Russ J Org Chem 56, 251–254 (2020). https://doi.org/10.1134/S1070428020020116

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  • DOI: https://doi.org/10.1134/S1070428020020116

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