Skip to main content
SpringerLink
Log in

Experimental and Theoretical Justification for the Regiospecific Cycloaddition of Levopimaric Acid to 2-Acetyl- or 2-(Methoxycarbonyl)-1,4-Benzoquinone

  • Published:
Chemistry of Natural Compounds Aims and scope

New 4a-quinopimaric acid derivatives were synthesized via a Diels–Alder reaction of levopimaric acid with 2-acetyl- or 2-(methoxycarbonyl)-1,4-benzoquinone and were characterized using elemental analysis and NMR spectroscopy. Thermodynamic and activation parameters of the Diels–Alder reactions of levopimaric acid and a model diene (7-isopropyl-1,2,3,4,4a,5-hexahydronaphthalene) with 2-acetyl- or 2-(methoxycarbonyl)-1,4-benzoquinone were calculated by density-functional theory in order to explain the observed regioselective cycloaddition.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. G. A. Tolstikov, T. G. Tolstikova, E. E. Shul'ts, S. E. Tolstikov, and M. V. Khvostov, Resinous Acids of Russian Conifers. Chemistry, Pharmacology [in Russian], Geo, Novosibirsk, 2011, 395 pp.

  2. G. F. Vafina, R. R. Fazlyev, F. Z. Galin, and L. V. Spirikhin, Zh. Org. Khim., 45 (4), 515 (2009); G. A. Tolstikov, E. E. Shults, T. Sh. Mukhametyanova, I. P. Baikova, and L. V. Spirikhin, Zh. Org. Khim., 29, 698 (1993).

  3. N. Ardabilchi, J. M. Bruce, and J. Khalafy, J. Sci. Islamic Repub. Iran, 11 (3), 195 (2000).

    CAS  Google Scholar 

  4. B. Kumar, S. M. Suryawanshi, and D. S. Bhakuni, Tetrahedron Lett., 36 (26), 4625 (1995).

    Article  CAS  Google Scholar 

  5. A. Mukhopadhyay, S. M. Ali, M. Husain, S. N. Suryawanshi, and D. S. Bhakuni, Tetrahedron Lett., 30 (14), 1853 (1989).

    Article  CAS  Google Scholar 

  6. G.-R. Cai, Z. Guan, and Y.-H. He, Synth. Commun., 41, 3016 (2011).

    Article  CAS  Google Scholar 

  7. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry. Part B: Reaction and Synthesis, Kluwer Academic/Plenum Publishers, 2001, 965 pp.

  8. M. F. Ansell, B. W. Nash, and D. A. Wilson, J. Chem. Soc., 3012 (1963).

  9. N. N. Vorozhtsov and V. P. Mamaev, Sbornik Statei Obshch. Khim., 1, 533 (1953).

    CAS  Google Scholar 

  10. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian 09, Revision C.01, Gaussian Inc., Wallingford, CT (2010).

  11. A. D. Becke, J. Chem. Phys., 98, 5648 (1993).

    Article  CAS  Google Scholar 

  12. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785 (1988).

    Article  CAS  Google Scholar 

  13. B. Miehlich, A. Savin, H. Stoll, and H. Preuss, Chem. Phys. Lett., 157, 200 (1989).

    Article  CAS  Google Scholar 

  14. A. D. McLean and G. S. Chandler, J. Chem. Phys., 72, 5639 (1980).

    Article  CAS  Google Scholar 

  15. S. S. Borisevich, I. Tsipisheva, A. V. Kovalskaya, and S. L. Khursan, J. Theor. Comput. Chem., 13 (6), 1450048 (2014); DOI: 10.1142/S0219633614500485

    Article  CAS  Google Scholar 

  16. J. Tomasi, B. Mennucci, and R. Cammi, Chem. Rev., 105, 2999 (2005)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgment

The work was sponsored by a Grant of the RF President for Leading Scientific Schools No. NSh-1700.2014.3.

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, 450054, Ufa, Prosp. Oktyabrya, 71, Russian

    G. F. Vafina, S. S. Borisevich, A. R. Uzbekov, A. I. Poptsov, L. V. Spirikhin & S. L. Khursan

Authors
  1. G. F. Vafina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. S. Borisevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. R. Uzbekov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. I. Poptsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. V. Spirikhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. L. Khursan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. F. Vafina.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2015, pp. 964–969.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vafina, G.F., Borisevich, S.S., Uzbekov, A.R. et al. Experimental and Theoretical Justification for the Regiospecific Cycloaddition of Levopimaric Acid to 2-Acetyl- or 2-(Methoxycarbonyl)-1,4-Benzoquinone. Chem Nat Compd 51, 1120–1125 (2015). https://doi.org/10.1007/s10600-015-1506-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-015-1506-2

Keywords

Search

Navigation