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.
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References
Money, T., Nat. Prod. Rep., 1985, vol. 2, p. 253.
Armstrong, E. and Lowry, T., J. Chem. Soc., 1902, vol. 81, p. 1441.
Money, T., Organic Synthesis: Theory and Applications, Hudlicky, T., Ed., Greenwich, CT: JAI, 1996, vol. 3, p. 1.
Chelucci, G., Chem. Soc. Rev., 2006, vol. 35, p. 1230.
Grošelj, U., Curr. Org. Chem., 2015, vol. 19, p. 2048.
Kovalev, V., Shokova, E., Shmailov, A., Vatsouro, I., and Tafeenko, V., Eur. J. Org. Chem., 2010, p. 3754.
Kim, D.K., Shokova, E.A., Tafeenko, V.A., and Kovalev, V.V., Russ. J. Org. Chem., 2014, vol. 50, p. 464.
Kim, J.K., Shokova, E.A., Tafeenko, V.A., and Kovalev, V.V., Beilstein J. Org. Chem., 2014, vol. 10, p. 2270.
Shokova, E.A., Kim, J.K., and Kovalev, V.V., Russ. J. Org. Chem., 2015, vol. 51, p. 755.
Kovalev, V., Shokova, E., Chertkov, V., and Tafeenko, V., Eur. J. Org. Chem., 2016, p. 1508.
Clark, R.L., Wenzel, B.T., and Wenzel, T.J., Tetrahedron: Asymmetry, 2013, vol. 24, p. 297.
Hedin-Dahlström, J., Rosengren-Holmberg, J.P., Legrand, S., Wikman, S., and Nicholls, I.A., J. Org. Chem., 2006, vol. 71, p. 4845.
Zárraga, O.M. and Miranda, M.A., J. Chil. Chem. Soc., 2003, vol. 48, no. 2, p. 39.
Wang, J., Li, P., Ni, C., Yan, H., and Zhong, R., Synth. Commun., 2013, vol. 43, p. 1543.
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.
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.
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.
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.
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.
Lewis, F.W., McCabe, T.C., and Grayson, D.H., Tetrahedron, 2011, vol. 67, p. 7517.
Lewis, F.W., Egron, G., and Grayson, D.H., Tetrahedron: Asymmetry, 2009, vol. 20, p. 1531.
Abrunhosa, L., Gulea, M., and Masson, S., Synthesis, 2004, p. 928.
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.
McNulty, J., Millar, M.J., Bernardinelli, G., and Jefford, Ch.W., J. Org. Chem., 1999, vol. 64, p. 5312.
Hofer, M., Strittmatter, H., and Sieber, V., ChemCatChem, 2013, vol. 5, p. 3351.
Butov, G.M., Mokhov, V.M., Parshin, G.Yu., and Kunaev, R.U., Russ. J. Org. Chem., 2009, vol. 45, p. 1864.
Khanvilkar, A.N., Gupta, R., and Bedecar, A.V., Indian J. Chem., Sect. B, 2015, vol. 54, p. 1327.
Xu, P.-F., Chen, Y.-S., Lin, S.-I., and Lu, T.-J., J. Org. Chem., 2002, vol. 67, p. 2309.
Martin, K.E., Bernard, T.G., Antony, B.M., and William, P.W., J. Chem. Soc., Perkin Trans. 1, 1991, p. 747.
Fleming, I. and Woodward, R.B., J. Chem. Soc. C, 1968, p. 1289.
Studer, A., Synthesis, 1996, p. 793.
Reetz, M.T., Angew. Chem., Int. Ed. Engl., 1991, vol. 30, p. 1531.
Lee, C.-L.K., Lee, C.-H.A., Tan, K.-T., and Loh, T.-P., Org. Lett., 2004, vol. 6, p. 1281.
Dmitrov, V., Simova, S., and Kostova, K., Tetrahedron, 1996, vol. 52, p. 1699.
Evans, M.D. and Kaye, P.T., S. Afr. J. Chem., 1998, vol. 51, p. 160.
Lobb, K.A. and Kaye, P.T., S. Afr. J. Chem., 2003, vol. 56, p. 60.
Fischer, N. and Opitz, G., Organic Syntheses, Baumgarten, H.E., Ed., New York: Wiley, 1973, collect. vol. 5, p. 877.
Vostrikov, N.S., Abutkov, A.V., Vasikov, V.Z., and Miftakhov, M.S., Russ. J. Org. Chem., 2003, vol. 39, p. 650.
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.
Knizhnikov, V.O., Voitenko, Z.V., Golovko, V.B., and Gorichko, M.V., Tetrahedron, 2012, vol. 68, p. 1972.
Kinzl, F.R. and Riepl, H.M., Helv. Chim. Acta, 2015, vol. 98, p. 447.
Biggs, R.A. and Ogilvie, W.W., Tetrahedron, 2013, vol. 69, p. 1539.
Grošelj, U., Sevšek, A., Ricko, S., Golobic, A., Svete, J., and Stanovnik, B., Chirality, 2012, vol. 24, p. 778.
Yang, T.-F., Zhang, Z.-N., Tseng, C.-H., and Chen, L.-H., Tetrahedron Lett., 2005, vol. 46, p. 1917.
Yang, T.-F., Tseng, C.-H., Shen, C.-H., Chen, L.-H., and Kao, L.-T., Tetrahedron, 2009, vol. 65, p. 9854.
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.
Thomas, A.A., Monk, K.A., Abraham, S., Lee, S., and Garner, Ch.M., Tetrahedron Lett., 2001, vol. 42, p. 2261.
Vostrikov, N.S., Abutkov, A.V., Spirikhin, L.V., Fatykhov, A.A., and Miftakhov, M.S., Russ. Chem. Bull., Int. Ed., 2001, p. 654.
Li, W.-D.Z. and Yang, Y.-R., Org. Lett., 2005, vol. 7, p. 3107.
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.
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.
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.
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.
Mikláš, R., Miklášová, N., Bukovský, M., and Devínsky, F., Acta Fac. Pharm. Univ. Comenianae, 2014, vol. 61, p. 42.
Mikláš, R., Miklášová, N., Bukovský, M., Horváth, B., Kubincová, J., and Devínsky, F., Eur. J. Pharm. Sci., 2014, vol. 65, p. 29.
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.
Stavrakov, G., Valcheva, V., Philipova, I., and Doytchinova, I., Eur. J. Med. Chem., 2013, vol. 70, p. 372.
Stavrakov, G., Philipova, I., Valcheva, V., and Momeko, G., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 165.
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.
Fernandes, T.A., Mendes, F., Roseiro, A.P.S., Santos, I., and Carvalho, M.F.N.N., Polyhedron, 2015, vol. 87, p. 215.
Hosny, M.A., El-Sayed, T.H., and El-Sawi, E.A., E-J. Chem., 2012, vol. 9, p. 1276.
Agrawal, S., Jain, J., Kumar, A., Gupta, P., and Garg, V., Res. Rep. Med. Chem., 2014, vol. 4, p. 47.
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.
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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.
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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
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DOI: https://doi.org/10.1134/S1070428016040011