Skip to main content
SpringerLink
Log in

Synthetic transformations of higher terpenoids: XXXVI. Synthesis of furanolabdanoid glycoconjugates with a 1,2,3-triazole linker

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Procedures have been developed for the synthesis of 16-[(propargyloxy)methyl]- and 7- and 18-(propargyloxy)labda-8(9),13,14-trienes from phlomisoic acid. Copper-catalyzed cycloaddition of the labdanoid alkynes to azido derivatives of α-D-glucose, D-galactose, D-xylose, and L-arabinose afforded the corresponding N-glycosyl-1,2,3-triazole conjugates.

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

Similar content being viewed by others

References

  1. Kharitonov, Yu.V., Shakirov, M.M., Pokrovskii, M.A., Pokrovskii, A.G., and Shults, E.E., Chem. Nat. Compd., 2017, vol. 53, p. 65.

    Article  Google Scholar 

  2. Shults, E.E., Mironov, M.E., and Kharitonov, Y.V., Chem. Nat. Compd., 2014, vol. 50, p. 2.

    Article  CAS  Google Scholar 

  3. Yang, Y., Gu, L., Xiao, Y., Liu, Q., Hu, H., Wang, Z., and Chen, K., PLoS One, 2015, vol. 10, p. 1.

    Google Scholar 

  4. Katagiry, M., Ohtani, K., Kasai, R., Yamasaki, K., Yang, C.R., and Tanaka, O., Phytochemistry, 1993, vol. 35, p. 439.

    Article  Google Scholar 

  5. Delazar, A., Moderassi, M., Shoeb, M., Nahar, L., Reid, R.G., Kumarasamy, Y., Majinda, R.T., and Sarker, S.D., Nat. Prod. Res., 2006, vol. 20, p. 167.

    Article  CAS  Google Scholar 

  6. Delazar, A., Modarresi, M., Nazemiyeh, H., Fathi-Azad, F., Nahar, L., and Sarker, S.D., Nat. Prod. Commun., 2008, vol. 3, p. 873.

    CAS  Google Scholar 

  7. Sudibya, H.G., Ma, J.M., Dong, X.C., Ng, S., Li, L.J., Liu, X.W., and Chen, P., Angew. Chem., Int. Ed., 2009, vol. 48, p. 2723.

    Article  CAS  Google Scholar 

  8. Jung, K.H., Muller, M., and Schmidt, R.R., Chem. Rev., 2000, vol. 100, p. 4423.

    Article  CAS  Google Scholar 

  9. Parida, P.K., Sau, A., Ghosh, T., Jana, K., Biswas, K., Raha, S., and Misra, A.K., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 3865.

    Article  CAS  Google Scholar 

  10. Cheng, K., Liu, J., Liu, X., Li, H., Sun, H., and Xie, J., Carbohydr. Res., 2009, vol. 344, p. 841.

    Article  CAS  Google Scholar 

  11. Cheng, K., Liu, J., Sun, H., Bokor, E., Czifrák, K., Kónya, B., Tóth, M., Docsa, T., Gergely, P., and Somsák, L., New J. Chem., 2010, vol. 34, p. 1450.

    Article  CAS  Google Scholar 

  12. Kharitonov, Yu.V., Shul’ts, E.E., Shakirov, M.M., Pokrovskii, M.A., Pokrovskii, A.G., and Tolstikov, G.A., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, p. 2046.

    Article  CAS  Google Scholar 

  13. Reta, G.F., Chiaramello, A.I., García, C., León, L.G., Martín, V.S., Padrón, J.M., Tonn, C.E., and Donadel, O.J., Eur. J. Med. Chem., 2013, vol. 67, p. 28.

    Article  CAS  Google Scholar 

  14. Pertino, M.W., Theoduloz, C., Bastías, M., and Schmeda-Hirschmann, G., Molecules, 2013, vol. 18, p. 5936.

    Article  Google Scholar 

  15. Mironov, M.E., Kharitonov, Yu.V., Shul’ts, E.E., Shakirov, M.M., Bagryanskaya, I.Yu., and Tolstikov, G.A., Chem. Nat. Compd., 2010, vol. 46, p. 233.

    Article  CAS  Google Scholar 

  16. Kharitonov, Yu.V., Shul’ts, E.E., Shakirov, M.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2009, vol. 45, p. 637.

    Article  CAS  Google Scholar 

  17. Kharitonov, Yu.V., Shul’ts, E.E., Gatilov, Yu.V., Bagryanskaya, I.Yu., Shakirov, M.M., and Tolstikov, G.A., Chem. Nat. Compd., 2012, vol. 48, p. 250.

    Article  CAS  Google Scholar 

  18. Mironov, M.E., Kharitonov, Yu.V., Shul’ts, E.E., Shakirov, M.M., Gatilov, Yu.V., and Tolstikov, G.A., Russ. J. Org. Chem., 2010, vol. 46, p. 1869.

    Article  CAS  Google Scholar 

  19. Salunke, S.B., Babu, N.S., and Chen, C.T., Chem. Commun., 2011, vol. 47, p. 10440.

    Article  CAS  Google Scholar 

  20. Kumar, R., Tiwari, P., Maulik, P.R., and Misra, A.K., Eur. J. Org. Chem., 2006, p. 74.

    Google Scholar 

  21. Nisic, F. and Bernardi, A., Carbohydr. Res., 2008, vol. 343, p. 1636.

    Article  CAS  Google Scholar 

  22. Tropper, F.D., Andersson, F.O., Braun, S., and Roy, R., Synthesis, 1992, p. 618.

    Google Scholar 

  23. Creary, X., Anderson, A., Brophy, C., Crowell, F., and Funk, Z., J. Org. Chem., 2012, vol. 77, p. 8756.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    O. I. Kremenko, Yu. V. Kharitonov & E. E. Shul’ts

Authors
  1. O. I. Kremenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. V. Kharitonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. E. Shul’ts
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. E. Shul’ts.

Additional information

Original Russian Text © O.I. Kremenko, Yu.V. Kharitonov, E.E. Shul’ts, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 1, pp. 42–52.

For communication XXXV, see [1].

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kremenko, O.I., Kharitonov, Y.V. & Shul’ts, E.E. Synthetic transformations of higher terpenoids: XXXVI. Synthesis of furanolabdanoid glycoconjugates with a 1,2,3-triazole linker. Russ J Org Chem 53, 35–46 (2017). https://doi.org/10.1134/S1070428017010079

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017010079

Search

Navigation