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Synthesis of Vinyl-Containing Lupane- and a-Secolupane-Type Triterpene Esters

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Chemistry of Natural Compounds Aims and scope

Vinyl-containing lupane- and oleanane-type C-3 and C-28 esters were synthesized from betulin and A-secotriterpene alcohols. The reaction of 2,3-secolupane alcohol 5 with vinylacetic acid produced ester 8 and a recyclization product, methyl 2β,3β-dihydroxylup-20(29)-en-28-oate (13), which was formed quantitatively in the reaction of 5 with maleic acid.

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Acknowledgment

The work was sponsored by the Basic Research Program, UB, RAS (No. 15-21-3-2) and RFBR Grant No. 15-03-01701_a.

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Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm, 614013, Russia

    G. F. Krainova, I. A. Tolmacheva, M. N. Gorbunova & V. V. Grishko

  2. B. N. Yel’tsin Ural Federal University, Ekaterinburg, 620002, Russia

    O. S. El’tsov

Authors
  1. G. F. Krainova
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  2. I. A. Tolmacheva
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  3. O. S. El’tsov
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  4. M. N. Gorbunova
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  5. V. V. Grishko
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Corresponding author

Correspondence to V. V. Grishko.

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Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2016, pp. 225–229.

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Krainova, G.F., Tolmacheva, I.A., El’tsov, O.S. et al. Synthesis of Vinyl-Containing Lupane- and a-Secolupane-Type Triterpene Esters. Chem Nat Compd 52, 256–261 (2016). https://doi.org/10.1007/s10600-016-1608-5

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  • DOI: https://doi.org/10.1007/s10600-016-1608-5

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