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Intramolecular cyclization involving O-vinyl or O-vinylketoxime function in a number of pentacyclic triterpenoids in superbasic medium

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Abstract

28-Triphenylmethoxylup-20(29)-ene-2,3-dione dioxime and 18α(H)-oleanane-3β,19β,28-triol upon reaction with acetylene in superbasic medium KOH-DMSO undergo intramolecular cyclization with the formation of products containing 1,2,5-oxadiazole and tetrahydrofuran fragment, respectively.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    A. V. Orlov, N. G. Komissarova, O. V. Shitikova, L. V. Spirikhin & M. S. Yunusov

Authors
  1. A. V. Orlov
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  2. N. G. Komissarova
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  3. O. V. Shitikova
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  4. L. V. Spirikhin
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  5. M. S. Yunusov
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Corresponding author

Correspondence to M. S. Yunusov.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0686–0690, March, 2013.

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Orlov, A.V., Komissarova, N.G., Shitikova, O.V. et al. Intramolecular cyclization involving O-vinyl or O-vinylketoxime function in a number of pentacyclic triterpenoids in superbasic medium. Russ Chem Bull 62, 687–691 (2013). https://doi.org/10.1007/s11172-013-0093-2

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  • DOI: https://doi.org/10.1007/s11172-013-0093-2

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