Skip to main content
SpringerLink
Log in

Pd-catalyzed synthesis of 2-alkynyl derivatives of 19β,28-epoxy-18α-olean-1-en-3-one

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

Abstract

Basing on Sonogashira reaction of 2-iodo-19β,28-epoxy-18α-olean-1-en-3-one with alkynes an effective approach was developed to the synthesis of 2-alkynyl derivatives of 19β,28-epoxy-18α-olean-1-en-3-one. Initial 2-iodo-19β,28-epoxy-18α-olean-1-en-3-one was obtained by isomerization of the accessible betulin into allobetulin in the presence of Amberlyst 15, oxidation of allobetulin to 19β,28-epoxy-18α-olean-1-en-3-one under the action of 2-iodoxybenzoic acid, and iodination of the obtained enone in the presence of DMAP.

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. Tolstikov, G.A., Flekhter, O.B., Shultz, E.E., Baltina, L.A., and Tolstikov, A.G., Chem. Sustain. Develop., 2005, vol. 13, p. 1.

    Article  CAS  Google Scholar 

  2. Alakurtti, S., Mäkelä, T., Koskimies, S., and Yli-Kauhaluoma, J., Eur. J. Pharm. Sci., 2006, vol. 29, p. 1.

    Article  CAS  Google Scholar 

  3. Tolstikova, T.G., Sorokina, I.V., Tolstikov, G.A., Tolstikov, A.G., and Flekhter, O.B., Russ. J. Bioorg. Chem., 2006, vol. 32, p. 261. doi 10.1134/S1068162006030083

    Article  CAS  Google Scholar 

  4. Dehaen, W., Mashentseva, A.A., and Seitembetov, T.S., Molecules, 2011, vol. 16, p. 2443.

    Article  CAS  Google Scholar 

  5. Aiken, C. and Chen, C.H., Trends Mol. Med., 2005, vol. 11, p. 31.

    Article  CAS  Google Scholar 

  6. Cichewicz, R.H. and Kouzi, S.A., Med. Res. Rev., 2004, vol. 24, p. 90.

    Article  CAS  Google Scholar 

  7. Zhang, D.-M., Xu, H.-G., Wang, L., Li, Y.-J., Sun, P.-H., Wu, X.-M., Wang, G.-J., Chen, W.-M., and Ye, W.-C., Med. Res. Rev., 2015, vol. 35, p. 1127.

    Article  Google Scholar 

  8. Csuk, R., Barthel, A., Kluge, R., Ströhl, D., Kommera, H., and Paschke, R., Bioorg. Med. Chem., 2010, vol. 18, p. 1344.

    Article  CAS  Google Scholar 

  9. Urban, M., Vlk, M., Dzubak, P., Hajduch, M., and Sarek, J., Bioorg. Med. Chem., 2012, vol. 20, p. 3666.

    Article  CAS  Google Scholar 

  10. You, Y.-J., Kim, Y., Nam, N.-H., and Ahn, B.-Z., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 3137.

    Article  CAS  Google Scholar 

  11. Mukherjee, R., Jaggi, M., Siddiqui, M.J.A., Srivastava, S.K., Rajendran, P., Vardhan, A., and Burman, A.C., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 4087.

    Article  CAS  Google Scholar 

  12. Pettit, G.R., Melody, N., Hempenstall, F., Chapuis, J.-C., Groy, T.L., and Williams, L., J. Nat. Prod., 2014, vol. 77, p. 863.

    Article  CAS  Google Scholar 

  13. Urban, M., Sarek, J., Klinot, J., Korinkova, G., and Hajduch, M., J. Nat. Prod., 2004, vol. 67, p. 1100.

    Article  CAS  Google Scholar 

  14. Urban, M., Sarek, J., Tislerova, I., Dzubak, P., and Hajduch, M., Bioorg. Med. Chem., 2005, vol. 13, p. 5527.

    Article  CAS  Google Scholar 

  15. Borkova, L., Jasikova, L., Rehulka, J., Frisonsova, K., Urban, M., Frydrych, I., Popa, I., Hajduch, M., Dickinson, N.J., Vlk, M., Dzubak, P., and Sarek, J., Eur. J. Med. Chem., 2015, vol. 96, p. 482.

    Article  CAS  Google Scholar 

  16. Csuk, R., Stark, S., Nitsche, C., Barthel, A., and Siewert, B., Eur. J. Med. Chem., 2012, vol. 53, p. 337.

    Article  CAS  Google Scholar 

  17. Dembitsky, V.M., Levitsky, D.O., Gloriozova, T.A., and Poroikov, V.V., Nat. Prod. Commun., 2006, vol. 1, p. 773.

    CAS  Google Scholar 

  18. Dembitsky, V.M., Lipids, 2006, vol. 41, p. 883.

    Article  CAS  Google Scholar 

  19. Siddiq, A. and Dembitsky, V., Anti-Cancer Agents Med. Chem., 2008, vol. 8, p. 132.

    Article  CAS  Google Scholar 

  20. Mejia, E.J., Magranet, L.B., De Voogd, N.J., TenDyke, K., Qiu, D., Shen, Y.Y., Zhou, Z., and Crews, P., J. Nat. Prod., 2013, vol. 76, p. 425. doi 10.1021/np3008446

    Article  CAS  Google Scholar 

  21. Zhou, Z.-F., Menna, M., Cai, Y.-S., and Guo, Y.-W., Chem. Rev., 2015, vol. 115, p. 1543.

    Article  CAS  Google Scholar 

  22. Csuk, R., Barthel, A., Kluge, R., and Ströhl, D., Bioorg. Med. Chem., 2010, vol. 18, p. 7252.

    Article  CAS  Google Scholar 

  23. Csuk, R., Barthel, A., Sczepek, R., Siewert, B., and Schwarz, S., Arch. Pharm. Chem. Life Sci., 2011, vol. 344, p. 37.

    Article  CAS  Google Scholar 

  24. Csuk, R., Nitsche, C., Sczepek, R., Schwarz, S., and Siewert, B., Arch. Pharm. Chem. Life Sci., 2013, vol. 346, p. 232.

    Article  CAS  Google Scholar 

  25. Csuk, R., Sczepek, R., Siewert, B., and Nitsche, C., Bioorg. Med. Chem., 2013, vol. 21, p. 425.

    Article  CAS  Google Scholar 

  26. Boryczka, S., Bębenek, E., Wietrzyk, J., Kempińska, K., Jastrzębska, M., Kusz, J., and Nowak, M., Molecules, 2013, vol. 18, p. 4526.

    Article  CAS  Google Scholar 

  27. Bębenek, E., Chrobak, E., Wietrzyk, J., Kadela, M., Chrobak, A., Kusz, J., Ksiązek, M., Jastrzębska, M., and Boryczka, S., J. Mol. Struct., 2016, vol. 1106, p. 210.

    Article  Google Scholar 

  28. Filippova, E.A., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Gen. Chem., 2013, vol. 83, p. 1633. doi 10.1134/S1070363213080306

    Article  CAS  Google Scholar 

  29. Frigerio, M., Santagostino, M., and Sputore, S., J. Org. Chem., 1999, vol. 64, p. 4537.

    Article  CAS  Google Scholar 

  30. Nicolaou, K.C., Zhong, Y.-L., and Baran, P.S., J. Am. Chem. Soc., 2000, vol. 122, p. 7596.

    Article  CAS  Google Scholar 

  31. Krafft, M.E. and Cran, J.W., Synlett., 2005, p. 1263.

    Google Scholar 

  32. Sholichin, M., Yamasaki, K., Kasai, R., and Tanaka, O., Chem. Pharm. Bull., 1980, vol. 28, p. 1006.

    Article  CAS  Google Scholar 

  33. Carpenter, R.C., Sotheeswaran, S., Sultanbawa, M.U.S., and Ternai, B., Org. Magn. Res., 1980, vol. 14, p. 462.

    Article  CAS  Google Scholar 

  34. Buděšínský, M. and Klinot, J., Coll. Czech. Chem. Commun., 1989, vol. 54, p. 1928.

    Article  Google Scholar 

  35. Heller, L., Obernauer, A., and Csuk, R., Bioorg. Med. Chem., 2015, vol. 23, p. 3002.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ufa State Petroleum Technological University, ul. Kosmonavtov 1, Ufa, 450062, Russia

    R. N. Shakhmaev, A. Sh. Sunagatullina, E. A. Abdullina & V. V. Zorin

Authors
  1. R. N. Shakhmaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Sh. Sunagatullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Abdullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Zorin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Zorin.

Additional information

Original Russian Text © R.N. Shakhmaev, A.Sh. Sunagatullina, E.A. Abdullina, V.V. Zorin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 11, pp. 1668–1672.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shakhmaev, R.N., Sunagatullina, A.S., Abdullina, E.A. et al. Pd-catalyzed synthesis of 2-alkynyl derivatives of 19β,28-epoxy-18α-olean-1-en-3-one. Russ J Org Chem 53, 1705–1709 (2017). https://doi.org/10.1134/S1070428017110173

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017110173

Search

Navigation