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Synthesis of a Triterpenoid with a 1,2,4,5-Tetraoxane Fragment

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Chemistry of Natural Compounds Aims and scope

Acid-catalyzed formation of the peroxyacetal of cyclohexanone bis-hydroperoxide and a triterpene ketone synthesized for the first time 19β,28-epoxy-28-oxo-18α-olean-3-spiro-6′-(1′,2′,4′,5′-tetraoxacyclohexane)-3′-spirocyclohexane, the structure of which was confirmed by NMR spectroscopy and an x-ray crystal structure analysis. 19β,28-Epoxy-28-oxo-18α-olean-1-en-3-one was formed as a side product during oxidative dehydration of 28-oxoallobetulone.

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Acknowledgment

The work was sponsored by the RFBR (Projects Nos. 09-03-00831 and 14-03-31664) and a grant of the Russian Federation President for State Support of Young Russian Scientists (MD-3852.2009.3).

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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

    E. Yu. Yamansarov, O. B. Kazakova, A. N. Lobov & D. V. Kazakov

  2. A. N. Nesmeyanov Institute of Elementorganic Compounds, Russian Academy of Sciences, Moscow, Russia

    K. Yu. Suponitskii

Authors
  1. E. Yu. Yamansarov
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  2. O. B. Kazakova
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  3. A. N. Lobov
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  4. D. V. Kazakov
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  5. K. Yu. Suponitskii
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Corresponding author

Correspondence to O. B. Kazakova.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2015, pp. 87–91.

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Yamansarov, E.Y., Kazakova, O.B., Lobov, A.N. et al. Synthesis of a Triterpenoid with a 1,2,4,5-Tetraoxane Fragment. Chem Nat Compd 51, 97–102 (2015). https://doi.org/10.1007/s10600-015-1211-1

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  • DOI: https://doi.org/10.1007/s10600-015-1211-1

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