Skip to main content
Log in

Synthesis of terpenophenols via direct alkylation of phenols by terpenes

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

Literature data on the alkylation of phenolic compounds by mono-, sesqui-, and diterpenes in the presence of various catalysts are reviewed.

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. F. M. Dean,Naturally Occurring Oxygen Ring Compounds, Butterworths, London (1963).

    Google Scholar 

  2. W. D. Ollis, ed.,Recent Developments in the Chemistry of Natural Phenolic Compounds, Proceedings of the Plant Phenolics Group Symposium, Symposium Publication Division, Pergamon Press, Oxford, New York (1961).

    Google Scholar 

  3. Terpenoids and Steroids. Specialist Periodical Report, The Chemical Society, London (1975–1977), Vols. 6–9.

  4. B. M. Howard, K. Clarkson, and R. L. Bernstein,Tetrahedron Lett., 4449 (1976).

  5. G. Rudali,C. R. Soc. Biol.,160, 1365 (1966/1967).

    Google Scholar 

  6. W. D. M. Paton, in:Annual Review of Pharmacology, H. W. Ellioth et al., ed, Annual Reviews Inc., Palo Alto (1975), p. 15.

    Google Scholar 

  7. G. V. Lazur'evskii and L. A. Nikolaeva,Cannabinoids [in Russian], Shtiintsa, Kishinev (1972).

    Google Scholar 

  8. K. Tunving,Acta Psychiatr. Scand.,72, 209 (1985).

    Google Scholar 

  9. J. Killenstein and S. A. Nelemans,Ned. Tijdschr. Geneeskd.,141, 1689 (1997).

    Google Scholar 

  10. G. Nahas,Bull. Narc.,29, 13 (1977).

    Google Scholar 

  11. M. E. Heim,Fortschr. Med.,100, 343 (1982).

    Google Scholar 

  12. W. Fenical, J. J. Sims, and D. Squatrido,J. Org. Chem.,38, 2383 (1973).

    Google Scholar 

  13. M. Shinohara, H. Kaise, Y. Nakano, T. Izawa, Y. Oshiro, and W. Miyazaki, Belg. Pat. No. 867,095;Chem. Abstr.,90, 168797x (1979).

    Google Scholar 

  14. M. Goodman and F. Morehouse,Organic Molecules in Action, 2nd Ed., Gordon and Breach, New York (1974).

    Google Scholar 

  15. V. M. Berezovskii,Chemistry of Vitamins [in Russian], Pishchepromizdat, Moscow (1972).

    Google Scholar 

  16. W. Gerwick and W. Fenical,J. Org. Chem.,46, 22 (1981).

    Google Scholar 

  17. H. Nohl, L. Gille, and K. Staniek,Mol. Aspects Med.,18, Suppl., S 33 (1997).

    Google Scholar 

  18. L. Ernster and G. Dallner,Biochim. Biophys. Acta,1271, 195 (1995).

    Google Scholar 

  19. M. D. Sutherland,Univ. Queensl. Pap. Dept. Chem.,1, 10 (1949).

    Google Scholar 

  20. M. H. Stern, T. H. Regan, D. P. Maier, C. D. Robeson, and J. G. Thweatt,J. Org. Chem.,38, No. 7, 1264 (1973).

    Google Scholar 

  21. E. Pottier and L. Savidan,Bull. Soc. Chim. Fr., No. 5–6, Part 2, 557 (1977).

    Google Scholar 

  22. K. L. Stevens, L. Jurd, and G. Manners,Tetrahedron,30, No. 14, 2075 (1974).

    Google Scholar 

  23. G. Manners, L. Jurd, and K. Stevens,Tetrahedron,28, 2949 (1972).

    Google Scholar 

  24. R. J. Mechoulam and B. Yagen,Tetrahedron Lett.,60, 5349 (1969).

    Google Scholar 

  25. T. Petrzilka, W. Haefliger, and C. Sikemeier,Helv. Chim. Acta,52, 1102 (1969).

    Google Scholar 

  26. B. Cardillo and L. Merlini,Gazz. Chim. Ital.,103, 127 (1973).

    Google Scholar 

  27. L. Crombie and R. Ponsford,Tetrahedron Lett.,48, 4557 (1968).

    Google Scholar 

  28. L. Crombie and R. Ponsford,J. Chem. Soc. C., No. 4, 788 (1971).

    Google Scholar 

  29. L. Crombie and R. Ponsford,J. Chem. Soc. C., No. 4, 796 (1971).

    Google Scholar 

  30. T. Ichikawa and T. Kato,Bull. Chem. Soc. Jpn.,41, No. 8, 1224 (1968).

    Google Scholar 

  31. E. C. Taylor, K. Lenard, and Y. Shvo,J. Am. Chem. Soc.,88, 367 (1966).

    Google Scholar 

  32. R. J. Mechoulam and Y. Gaoni,J. Am. Chem. Soc.,88, 5673 (1966).

    Google Scholar 

  33. L. Crombie, S. D. Redshaw, D. A. Slack, and D. A. Whiting,J. Chem. Soc. C., No. 14, 628 (1979).

    Google Scholar 

  34. W. M. Bandaranayake, L. Crombie, and D. A. Whiting,J. Chem. Soc. C, No. 4, 804 (1971).

    Google Scholar 

  35. L. A. Kheifits, “Synthesis of terpenyl- and alkylphenols and preparation of fragrances from them” Author's Abstract of a Doctoral Dissertation in Chemical Sciences, Moscow (1986), p. 3.

  36. A. Costero and E. Melendez,Rev. Acad. Cienc. Exactas. Fis.-Quim. Nat. Zaragoza,33, 111 (1978).

    Google Scholar 

  37. V. V. Fomenko, D. V. Korchagina, N. F. Salakhutdinov, I. Yu. Bagryanskaya, Yu. V. Gatilov, K. G. Ione, and V. A. Barkhash,Zh. Org. Khim.,34, (1998).

  38. L. A. Kheifits and V. M. Dashunin,Fragrances and Other Products for Perfumery [in Russian], Khimiya, Moscow 1994).

    Google Scholar 

  39. R. J. Mechoulam and Y. Gaoni,Fortschr. Chem. Org. Naturst.,25, 175–213 (1967).

    Google Scholar 

  40. G. B. Uliss, G. R. Handrick, H. C. Dalzell, and R. K. Razdan,J. Am. Chem. Soc.,100, 2929 (1978).

    Google Scholar 

  41. U. Kraatz, H. Wolfers, A. Kraatz, and F. Korte,Chem. Ber.,110, 1776 (1977).

    Google Scholar 

  42. K. Matsumoto, P. Stark, and R. G. Meister,J. Med. Chem.,20, 17 (1977).

    Google Scholar 

  43. S.-H. Baek,J. Chem. Res., Synop.,12, 45 (1994).

    Google Scholar 

  44. R. Ghosh, A. R. Todd, and G. C. Wright,J. Chem. Soc., 137 (1941).

  45. O. Isler and M. Montavon,Bull. Soc: Chim. Fr.,5, 2403 (1965).

    Google Scholar 

  46. Y. Ichikawa, Y. Yamanaka, M. Yamamoto, T. Takeshita, and T. Niki, Jpn. Pat. No. 74 42,676;Chem. Abstr.,81, 152455 (1974).

    Google Scholar 

  47. G. B. Elyakov and V. A. Stonik,Terpenoids of Marine Organisms [in Russian], Nauka, Moscow (1986).

    Google Scholar 

  48. A. I. Usov and O. S. Chizhov,Chemical Investigations of Algae [in Russian], Znanie, Moscow (1988), Vol. 5.

    Google Scholar 

  49. A. Gonzalez Gonzalez and J. Delgado Martin,Tetrahedron Lett., No. 22, 2259 (1972).

    Google Scholar 

  50. A. Gonzalez Gonzalez, J. Delgado Martin, and M. L. Rodriguez,Anal. Quim.,72, 1004 (1976).

    Google Scholar 

  51. E. V. Kuzakov and E. N. Shmidt,Khim. Prir. Soedin., 653 (1998).

Download references

Authors

Additional information

Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, fax (3832) 34 47 52, e-mail: shreed@nioch.nsc.ru. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 198–207, May–June, 2000.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kuzakov, E.V., Shmidt, E.N. Synthesis of terpenophenols via direct alkylation of phenols by terpenes. Chem Nat Compd 36, 245–257 (2000). https://doi.org/10.1007/BF02238328

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02238328

Key words

Navigation