Chemistry of Natural Compounds

, Volume 54, Issue 1, pp 88–91 | Cite as

Synthesis of New Methoxyquinopimaric-Acid Scaffold Derivatives

  • G. F. Vafina
  • A. I. Poptsov
  • L. V. Spirikhin
  • F. Z. Galin

New 2- and 3-methoxyquinopimaric-acid derivatives were synthesized by a Diels–Alder reaction of levopimaric acid and 2-methoxy-1,4-benzoquinone. The reaction rate and regioselectivity of the cycloaddition were increased significantly by using a Bmim·BF4 catalyst. Photolysis of 3-methoxyquinopimaric acid produced new scaffold derivatives. The compounds were characterized by NMR spectroscopy and elemental analysis.


diene synthesis methoxyquinopimaric acid photocyclization 


  1. 1.
    G. A. Tolstikov, T. G. Tolstikova, E. E. Shults, S. E. Tolstikov, and M. V. Khvostov, Resin Acids of Russian Conifers. Chemistry and Pharmacology [in Russian], Geo, Novosibirsk, 2011, 395 pp.Google Scholar
  2. 2.
    G. F. Vafina, A. R. Uzbekov, V. V. Zarubaev, L. A. Karpinskaya, A. A. Shtro, and M. S. Yunusov, Chem. Nat. Compd., 51, 103 (2015).CrossRefGoogle Scholar
  3. 3.
    G. F. Vafina, A. R. Uzbekov, S. F. Gabdrakhmanova, N. S. Makara, F. S. Zarudii, and F. Z. Galin, Chem. Nat. Compd., 52, 82 (2016).CrossRefGoogle Scholar
  4. 4.
    G. F. Vafina, R. R. Fazlyev, F. Z. Galin, and L. V. Spirikhin, Russ. J. Org. Chem., 45, 500 (2009).CrossRefGoogle Scholar
  5. 5.
    A. R. Uzbekov, G. F. Vafina, A. N. Lobov, F. Z. Galin, and M. S. Yunusov, Russ. J. Org. Chem., 48 (4), 505 (2012).CrossRefGoogle Scholar
  6. 6.
    G. F. Vafina, R. R. Fazlyev, A. N. Lobov, L. V. Spirikhin, and F. Z. Galin, Russ. J. Org. Chem., 46 (9), 1364 (2010).CrossRefGoogle Scholar
  7. 7.
    R. V. Kuzmich, G. F. Vafina, F. Z. Galin, and M. S. Yunusov, Vestn. Bashk. Gos. Univ., 4, 1140 (2011).Google Scholar
  8. 8.
    I. S. Ioffe and A. F. Sukhina, Zh. Obshch. Khim., 23, 295 (1953).Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • G. F. Vafina
    • 1
  • A. I. Poptsov
    • 1
  • L. V. Spirikhin
    • 1
  • F. Z. Galin
    • 1
  1. 1.Ufa Institute of Chemistry, Russian Academy of SciencesUfaRussia

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