Skip to main content
Log in

Camphor and its derivatives. Unusual transformations and biological activity

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

Abstract

The review summarizes and analyzes data on unusual transformations of camphor and its derivatives, reported in the past 20 years. The results of studying biological activity of compounds containing a camphor fragment are also given.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Money, T., Nat. Prod. Rep., 1985, vol. 2, p. 253.

    Article  CAS  Google Scholar 

  2. Armstrong, E. and Lowry, T., J. Chem. Soc., 1902, vol. 81, p. 1441.

    Article  CAS  Google Scholar 

  3. Money, T., Organic Synthesis: Theory and Applications, Hudlicky, T., Ed., Greenwich, CT: JAI, 1996, vol. 3, p. 1.

    Article  CAS  Google Scholar 

  4. Chelucci, G., Chem. Soc. Rev., 2006, vol. 35, p. 1230.

    Article  CAS  Google Scholar 

  5. Grošelj, U., Curr. Org. Chem., 2015, vol. 19, p. 2048.

    Article  Google Scholar 

  6. Kovalev, V., Shokova, E., Shmailov, A., Vatsouro, I., and Tafeenko, V., Eur. J. Org. Chem., 2010, p. 3754.

    Google Scholar 

  7. Kim, D.K., Shokova, E.A., Tafeenko, V.A., and Kovalev, V.V., Russ. J. Org. Chem., 2014, vol. 50, p. 464.

    Article  CAS  Google Scholar 

  8. Kim, J.K., Shokova, E.A., Tafeenko, V.A., and Kovalev, V.V., Beilstein J. Org. Chem., 2014, vol. 10, p. 2270.

    Article  Google Scholar 

  9. Shokova, E.A., Kim, J.K., and Kovalev, V.V., Russ. J. Org. Chem., 2015, vol. 51, p. 755.

    Article  CAS  Google Scholar 

  10. Kovalev, V., Shokova, E., Chertkov, V., and Tafeenko, V., Eur. J. Org. Chem., 2016, p. 1508.

    Google Scholar 

  11. Clark, R.L., Wenzel, B.T., and Wenzel, T.J., Tetrahedron: Asymmetry, 2013, vol. 24, p. 297.

    Article  CAS  Google Scholar 

  12. Hedin-Dahlström, J., Rosengren-Holmberg, J.P., Legrand, S., Wikman, S., and Nicholls, I.A., J. Org. Chem., 2006, vol. 71, p. 4845.

    Article  Google Scholar 

  13. Zárraga, O.M. and Miranda, M.A., J. Chil. Chem. Soc., 2003, vol. 48, no. 2, p. 39.

    Article  Google Scholar 

  14. Wang, J., Li, P., Ni, C., Yan, H., and Zhong, R., Synth. Commun., 2013, vol. 43, p. 1543.

    Article  CAS  Google Scholar 

  15. Maroto, B.L., de la Moya Cerero, S., Martinez, A.G., Fraile, A.G., and Vilar, E.T., Tetrahedron: Asymmetry, 2000, vol. 11, p. 3059.

    Article  Google Scholar 

  16. Martinez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., and Maroto, B.L., Tetrahedron: Asymmetry, 2000, vol. 11, p. 4437.

    Article  Google Scholar 

  17. Martinez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., and Maroto, B.L., Tetrahedron Lett., 2001, vol. 42, p. 5017.

    Article  Google Scholar 

  18. Martinez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., and Maroto, B.L., Tetrahedron Lett., 2002, vol. 43, p. 1183.

    Article  Google Scholar 

  19. De la Moya Cerero, S., Martinez, A.G., Vilar, E.T., Fraile, A.G., and Maroto, B.L., J. Org. Chem., 2003, vol. 68, p. 1451.

    Article  Google Scholar 

  20. Lewis, F.W., McCabe, T.C., and Grayson, D.H., Tetrahedron, 2011, vol. 67, p. 7517.

    Article  CAS  Google Scholar 

  21. Lewis, F.W., Egron, G., and Grayson, D.H., Tetrahedron: Asymmetry, 2009, vol. 20, p. 1531.

    Article  CAS  Google Scholar 

  22. Abrunhosa, L., Gulea, M., and Masson, S., Synthesis, 2004, p. 928.

    Google Scholar 

  23. Khalilov, L.M., Parfenova, L.V., Pechatkina, S.V., Ibragimov, A.G., Genet, J.P., Dzhemilev, U.M., and Beletskaya, I.P., J. Organomet. Chem., 2004, vol. 689, p. 444.

    Article  CAS  Google Scholar 

  24. McNulty, J., Millar, M.J., Bernardinelli, G., and Jefford, Ch.W., J. Org. Chem., 1999, vol. 64, p. 5312.

    Article  CAS  Google Scholar 

  25. Hofer, M., Strittmatter, H., and Sieber, V., ChemCatChem, 2013, vol. 5, p. 3351.

    Article  CAS  Google Scholar 

  26. Butov, G.M., Mokhov, V.M., Parshin, G.Yu., and Kunaev, R.U., Russ. J. Org. Chem., 2009, vol. 45, p. 1864.

    Article  CAS  Google Scholar 

  27. Khanvilkar, A.N., Gupta, R., and Bedecar, A.V., Indian J. Chem., Sect. B, 2015, vol. 54, p. 1327.

    Google Scholar 

  28. Xu, P.-F., Chen, Y.-S., Lin, S.-I., and Lu, T.-J., J. Org. Chem., 2002, vol. 67, p. 2309.

    Article  CAS  Google Scholar 

  29. Martin, K.E., Bernard, T.G., Antony, B.M., and William, P.W., J. Chem. Soc., Perkin Trans. 1, 1991, p. 747.

    Google Scholar 

  30. Fleming, I. and Woodward, R.B., J. Chem. Soc. C, 1968, p. 1289.

    Google Scholar 

  31. Studer, A., Synthesis, 1996, p. 793.

    Google Scholar 

  32. Reetz, M.T., Angew. Chem., Int. Ed. Engl., 1991, vol. 30, p. 1531.

    Article  Google Scholar 

  33. Lee, C.-L.K., Lee, C.-H.A., Tan, K.-T., and Loh, T.-P., Org. Lett., 2004, vol. 6, p. 1281.

    Article  CAS  Google Scholar 

  34. Dmitrov, V., Simova, S., and Kostova, K., Tetrahedron, 1996, vol. 52, p. 1699.

    Article  Google Scholar 

  35. Evans, M.D. and Kaye, P.T., S. Afr. J. Chem., 1998, vol. 51, p. 160.

    CAS  Google Scholar 

  36. Lobb, K.A. and Kaye, P.T., S. Afr. J. Chem., 2003, vol. 56, p. 60.

    CAS  Google Scholar 

  37. Fischer, N. and Opitz, G., Organic Syntheses, Baumgarten, H.E., Ed., New York: Wiley, 1973, collect. vol. 5, p. 877.

    Google Scholar 

  38. Vostrikov, N.S., Abutkov, A.V., Vasikov, V.Z., and Miftakhov, M.S., Russ. J. Org. Chem., 2003, vol. 39, p. 650.

    Article  CAS  Google Scholar 

  39. Martinez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., de Oro Osuna, S., and Maroto, B.L., Tetrahedron Lett., 2001, vol. 42, p. 7795.

    Article  Google Scholar 

  40. Knizhnikov, V.O., Voitenko, Z.V., Golovko, V.B., and Gorichko, M.V., Tetrahedron, 2012, vol. 68, p. 1972.

    Article  CAS  Google Scholar 

  41. Kinzl, F.R. and Riepl, H.M., Helv. Chim. Acta, 2015, vol. 98, p. 447.

    Article  CAS  Google Scholar 

  42. Biggs, R.A. and Ogilvie, W.W., Tetrahedron, 2013, vol. 69, p. 1539.

    Article  CAS  Google Scholar 

  43. Grošelj, U., Sevšek, A., Ricko, S., Golobic, A., Svete, J., and Stanovnik, B., Chirality, 2012, vol. 24, p. 778.

    Article  Google Scholar 

  44. Yang, T.-F., Zhang, Z.-N., Tseng, C.-H., and Chen, L.-H., Tetrahedron Lett., 2005, vol. 46, p. 1917.

    Article  CAS  Google Scholar 

  45. Yang, T.-F., Tseng, C.-H., Shen, C.-H., Chen, L.-H., and Kao, L.-T., Tetrahedron, 2009, vol. 65, p. 9854.

    Article  CAS  Google Scholar 

  46. Martinez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., Maroto, B.L., and Morillo, C.D., Tetrahedron Lett., 2001, vol. 42, p. 8293.

    Article  Google Scholar 

  47. Thomas, A.A., Monk, K.A., Abraham, S., Lee, S., and Garner, Ch.M., Tetrahedron Lett., 2001, vol. 42, p. 2261.

    Article  CAS  Google Scholar 

  48. Vostrikov, N.S., Abutkov, A.V., Spirikhin, L.V., Fatykhov, A.A., and Miftakhov, M.S., Russ. Chem. Bull., Int. Ed., 2001, p. 654.

    Google Scholar 

  49. Li, W.-D.Z. and Yang, Y.-R., Org. Lett., 2005, vol. 7, p. 3107.

    Article  CAS  Google Scholar 

  50. Zhao, X., Zhang, Z.-W., Cui, W., Chen, S., Zhou, Y., Dong, J., Jie, Y., Wan, J., Xu, Y., and Hu, W., Med. Chem. Commun., 2015, vol. 6, p. 727.

    Article  CAS  Google Scholar 

  51. Martinez, A.G., Vilar, E.T., Fraile, A.G, de la Moya Cerero S., Rodriguez Herrero, M.E., Martinez, R.P., Subramanian, L.R., and Gancedo, A.G., J. Med. Chem., 1995, vol. 38, p. 4474.

    Article  Google Scholar 

  52. Zarubaev, V.V., Garshinina, A.V., Tretiak, T.S., Fedorova, V.A., Shtro, A.A., Sokolova, A.S., Yarovaya, O.I., and Salakhutdinov, N.F., Antiviral Res., 2015, vol. 120, p. 126.

    Article  CAS  Google Scholar 

  53. Sokolova, A.S., Yarovaya, O.I., Shernyukov, A.V., Pokrovsky, M.A., Pokrovsky, A.G., Lavrinenko, V.A., Zarubaev, V.V., Tretiak, T.S., Anfimov, P.M., Kiselev, O.I., Beklemishev, A.B., and Salakhutdinov, N.F., Bioorg. Med. Chem., 2013, vol. 21, p. 6690.

    Article  CAS  Google Scholar 

  54. Mikláš, R., Miklášová, N., Bukovský, M., and Devínsky, F., Acta Fac. Pharm. Univ. Comenianae, 2014, vol. 61, p. 42.

    Google Scholar 

  55. Mikláš, R., Miklášová, N., Bukovský, M., Horváth, B., Kubincová, J., and Devínsky, F., Eur. J. Pharm. Sci., 2014, vol. 65, p. 29.

    Article  Google Scholar 

  56. Petkova, Z., Valcheva, V., Momekov, G., Petrov, P., Dimitrov, V., Doytchinova, I., Stavrakov, G., and Stoyanova, M., Eur. J. Med. Chem., 2014, vol. 81, p. 150.

    Article  CAS  Google Scholar 

  57. Stavrakov, G., Valcheva, V., Philipova, I., and Doytchinova, I., Eur. J. Med. Chem., 2013, vol. 70, p. 372.

    Article  CAS  Google Scholar 

  58. Stavrakov, G., Philipova, I., Valcheva, V., and Momeko, G., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 165.

    Article  CAS  Google Scholar 

  59. Gillespie, P., Pietranico-Cole, S., Myers, M., Bilotta, J.A., Conde-Knape, K., Fotouhi, N., Goodnow, R.A., Jr., Guertin, K.R., Hamilton, M.M., Haynes, N.-E., Liu, B., Qi, L., Ren, Y., Scott, N.R., So, S.-S., Spence, C., Taub, R., Thakkar, K., Tilley, J.W., and Zwingelstein, C., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 2707.

    Article  CAS  Google Scholar 

  60. Fernandes, T.A., Mendes, F., Roseiro, A.P.S., Santos, I., and Carvalho, M.F.N.N., Polyhedron, 2015, vol. 87, p. 215.

    Article  CAS  Google Scholar 

  61. Hosny, M.A., El-Sayed, T.H., and El-Sawi, E.A., E-J. Chem., 2012, vol. 9, p. 1276.

    Article  CAS  Google Scholar 

  62. Agrawal, S., Jain, J., Kumar, A., Gupta, P., and Garg, V., Res. Rep. Med. Chem., 2014, vol. 4, p. 47.

    CAS  Google Scholar 

  63. Sokolova, A.S., Morozova, E.A., Vasilev, V.G., Yarovaya, O.I., Tolstikova, T.G., and Salakhutdinov, N.F., Russ. J. Bioorg. Chem., 2015, vol. 41, no. 2, p. 178.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. A. Shokova.

Additional information

Original Russian Text © E.A. Shokova, J.K. Kim, V.V. Kovalev, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 4, pp. 471–499.

El’vira Aleksandrovna Shokova was born in Moscow. She graduated from the Faculty of Chemistry, Moscow State University, and finished post-graduate courses at the faculty. Candidate of chemical sciences. Author of more than 170 publications, 16 USSR Inventor’s Certificates, and 2 RF patents. Leading researcher at the Faculty of Chemistry, Moscow State University. Fields of scientific interest: polyfunctional compounds, their synthesis and uses in organic synthesis; chemistry of adamantane and its derivatives; biologically active compounds.

Jung Keun Kim was born in 1980 in Seoul (Korea). In 2007 he graduated from the Faculty of Chemistry, Moscow State University, and in 2015 finished post-graduate courses thereat. Candidate of chemical sciences since 2015. Since 2008 till 2012 he worked as researcher at LG Chem and LG Hausys (Korea). Since 2015, J.K. Kim lives in China and works at the College of Chemistry and Molecular Engineering, Zhengzhou University. Fields of scientific interest: polycarbonyl compounds and their possible applications; chemistry of adamantane and its derivatives.

Vladimir Vasil’evich Kovalev was born in 1952 in Moscow oblast. In 1974 he graduated from the Faculty of Chemistry, Moscow State University, and then finished post-graduate courses at the faculty. Doctor of chemical sciences since 1991. Head of the Macrocyclic Receptor Laboratory at the Faculty of Chemistry, Moscow State University, since 2001. Fields of scientific interest: organic and supramolecular chemistry.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shokova, E.A., Kim, J.K. & Kovalev, V.V. Camphor and its derivatives. Unusual transformations and biological activity. Russ J Org Chem 52, 459–488 (2016). https://doi.org/10.1134/S1070428016040011

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428016040011

Keywords

Navigation