Skip to main content
Log in

Synthesis of 10-Carbonyl and 10-Carboxylic Derivatives of para-Mentha-1,8-Diene-5,6-Diol

  • Published:
Chemistry of Natural Compounds Aims and scope

The synthesis of 10-carbonyl and 10-carboxylic derivatives of para-mentha-1,8-diene-5,6-diol (1) that exhibited high anti-Parkinson’s activity was described. The synthesis of these compounds was an important programmatic component in a study of the metabolism of 1.

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

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Similar content being viewed by others

Explore related subjects

Discover the latest articles and news from researchers in related subjects, suggested using machine learning.

References

  1. O. V. Ardashov, A. V. Pavlova, I. V. Il’ina, E. A. Morozova, D. V. Korchagina, E. V. Karpova, K. P. Volcho, T. G. Tolstikova, and N. F. Salakhutdinov, J. Med. Chem., 54 (11), 3866 (2011).

    Article  CAS  PubMed  Google Scholar 

  2. T. G. Tolstikova, A. V. Pavlova, E. A. Morozova, O. V. Ardashov, I. V. Il’ina, K. P. Volcho, N. F. Salakhutdinov, and G. A. Tolstikov, Dokl. Akad. Nauk Fiziol., 435 (5), 708 (2010).

    Google Scholar 

  3. O. V. Ardashov, A. V. Pavlova, D. V. Korchagina, K. P. Volcho, T. G. Tolstikova, and N. F. Salakhutdinov, Med. Chem., 9 (5), 731 (2013).

    Article  CAS  PubMed  Google Scholar 

  4. W. Engel, J. Agric. Food Chem., 49, 4069 (2001).

    Article  CAS  PubMed  Google Scholar 

  5. T. Ishida, M. Toyota, and Y. Asakawa, Xenobiotica, 19, 843 (1989).

    Article  CAS  PubMed  Google Scholar 

  6. J. W. Regan and L. F. Bjeldanes, J. Agric. Food Chem., 24 (2), 4069 (1976).

    Article  Google Scholar 

  7. M. Yazawa, M. Shindo, and T. Shimada, Drug Metab. Dispos., 30 (5), 602 (2002).

    Article  Google Scholar 

  8. O. V. Ardashov, A. V. Pavlova, D. V. Korchagina, K. P. Volcho, T. G. Tolstikova, and N. F. Salakhutdinov, Bioorg. Med. Chem., 21 (5), 1082 (2013).

    Article  CAS  PubMed  Google Scholar 

  9. O. V. Ardashov, E. V. Khaid, O. S. Mikhal’chenko, D. V. Korchagina, K. P. Volcho, and N. F. Sakakhutdinov, Izv. Akad. Nauk, Ser. Khim., 62 (1), 172 (2013) [O. V. Ardashov, E. V. Khaid, O. S. Mikhal’chenko, D. V. Korchagina, K. P. Volcho, and N. F. Salakhutdinov, Russ. Chem. Bull., 62 (1), 171 (2013)].

    Google Scholar 

  10. O. V. Ardashov, K. P. Volcho, and N. F. Salakhutdinov, Usp. Khim., 83 (4), 281 (2014) [O. V. Ardashov, K. P. Volcho, and N. F. Salakhutdinov, Russ. Chem. Rev., 83 (4), 281 (2014)].

    Article  Google Scholar 

  11. M. von Montavon, H. Lindlar, R. Marbet, R. Ruegg, G. Ryser, G. Saucy, P. Zeller, and O. Isler, Helv. Chim. Acta, 49 (140), 1250 (1957).

    Article  Google Scholar 

  12. E. Vedejs, D. M. Gapinski, and J. P. Hagen, J. Org. Chem., 46, 5452 (1981).

    Article  Google Scholar 

  13. D. Xu, T. M. Penning, I. A. Blair, and R. G. Harvey, J. Org. Chem., 74 (2), 597 (2009).

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  14. A. G. Godfrey and B. Ganem, Tetrahedron Lett., 31 (34), 4825 (1990).

    Article  CAS  Google Scholar 

  15. M. Miyashita, A. Yoshikoshi, and P. A. Grieco, J. Org. Chem., 42 (23), 3772 (1977).

    Article  CAS  Google Scholar 

  16. M. Isobe, H. Iio, T. Kawai, and T. Goto, J. Am. Chem. Soc., 100 (6), 1942 (1978).

    Article  Google Scholar 

  17. T. Mineno, Tetrahedron Lett., 43, 7975 (2002).

    Article  CAS  Google Scholar 

  18. I. E. Marco, A. Ates, B. Augustyns, A. Gautier, Y. Quesnel, L. Turet, and M. Wiaux, Tetrahedron Lett., 40, 5613 (1999).

    Article  Google Scholar 

  19. F. A. Gimalova, G. M. Khalikova, S. A. Torosyan, D. Z. Akhmetshina, and M. S. Miftakhov, Zh. Org. Khim., 48 (2), 194 (2012) [F. A. Gimalova, G. M. Khalikova, S. A. Torosyan, D. Z. Akhmetshina, and M. S. Miftakhov, Russ. J. Org. Chem., 48 (2), 180 (2012)].

    Google Scholar 

  20. S. B. Balkrishna, E. C. Wayne, and H. W. Pinnick, Tetrahedron, 37, 2091 (1981).

    Article  Google Scholar 

  21. I. A. Pearl, J. Am. Chem. Soc., 68, 429 (1946).

    Article  CAS  PubMed  Google Scholar 

  22. Q. Wang, S. Y. Fan, H. N. C. Wong, Z. Li, B. M. Fung, R. J. Twieg, and H. T. Nguyen, Tetrahedron, 49 (3), 619 (1993).

    Article  CAS  Google Scholar 

  23. M. Kawaguchi, O. Hayashi, N. Sakai, M. Hamada, Y. Yamamoto, and J. Oda, Agric. Biol. Chem., 50 (12), 3107 (1986).

    Article  CAS  Google Scholar 

  24. T. Kitahara, A. Horiguchi, and K. Mori, Tetrahedron, 44 (15), 4713 (1988).

    Article  CAS  Google Scholar 

  25. X. Cong and Z.-J. Yao, J. Org. Chem., 71, 5365 (2006).

    Article  CAS  PubMed  Google Scholar 

  26. Q. Yang, C. Draghici, J. T. Njardarson, F. Li, B. R. Smith, and P. Das, Org. Biomol. Chem., 12, 330 (2014).

    Article  PubMed Central  PubMed  Google Scholar 

  27. D. Askin, C. Angst, and S. Danishefsky, J. Org. Chem., 52, 622 (1987).

    Article  CAS  Google Scholar 

  28. R. R. Gowda and D. Chakraborty, Chin. J. Chem., 29, 2379 (2011).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

We thank the Russian Federation Ministry of Education and Science for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to O. V. Ardashov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2015, pp. 419–423.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ardashov, O.V., Korchagina, D.V., Volcho, K.P. et al. Synthesis of 10-Carbonyl and 10-Carboxylic Derivatives of para-Mentha-1,8-Diene-5,6-Diol. Chem Nat Compd 51, 483–487 (2015). https://doi.org/10.1007/s10600-015-1320-x

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-015-1320-x

Keywords