Abstract
The review discusses recent advances in the field of acid-catalyzed intra- and intermolecular transformations of pinane terpenoids and their oxygen-containing derivatives.
Similar content being viewed by others
References
Masui, M. and Shioiri, T., Tetrahedron, 1995, vol. 51, p. 8363.
Khomenko, T.M., Salomatina, O.V., Kurbakova, S.Yu., Il’ina, I.V., Volcho, K.P., Komarova, N.I., Korchagina, D.V., Salakhutdinov, N.F., and Tolstikov, A.G., Russ. J. Org. Chem., 2006, vol. 42, p. 1653.
Malhotra, S.V. and Wang, Y., Tetrahedron: Asymmetry, 2006, vol. 17, p. 1032.
Szakonyi, Z., Balazs, A., Martinek, T.A., and Fulop, F., Tetrahedron: Asymmetry, 2006, vol. 17, p. 199.
Volcho, K.P., Rogoza, L.N., Salakhutdinov, N.F., Tolstikov, A.G., and Tolstikov, G.A., Preparativnaya khimiya terpenoidov. Chast’ 1. Bitsiklicheskie monoterpenoidy (Preparative Chemistry of Terpenoids. Part 1. Bicyclic Monoterpenoids), Novosibirsk: Sib. Otd. Ross. Akad. Nauk, 2005.
Corvi Mora, P. and Ranise, A., US Patent no. 6649658, 2003; Chem. Abstr., 2000, vol. 133,no. 310030.
Allison, J.D., Borden, J.H., McIntosh, R.L., de Groot, P., and Gries, R., J. Chem. Ecol., 2001, vol. 27, p. 633.
Hölderich, W.F. and Barsnick, U., Fine Chemicals through Heterogeneous Catalysis, Sheldon, R.A. and van Bekkum, H., Eds., Weinheim: Wiley, 2001, p. 223.
Erman, W.F., Chemistry of the Monoterpenes. Part B, New York: Marcel Dekker, 1985, p. 929.
Salakhutdinov, N.F. and Barkhash, V.A., Usp. Khim., 1997, vol. 66, p. 376.
Swift, K.A.D., Fine Chemicals through Heterogeneous Catalysis, Sheldon, R.A. and van Bekkum, H., Eds., Weinheim: Wiley, 2001, p. 242.
Swift, K.A.D., Top. Catal., 2004, vol. 27, p. 143.
Williams, C.M. and Whittaker, D., J. Chem. Soc. B, 1971, p. 668.
Valkanas, G.N., J. Org. Chem., 1976, vol. 41, p. 1179.
Williams, C.M. and Whittaker, D., J. Chem. Soc. B, 1971, p. 672.
Ericson, G.W. and Fry, J.L.J., J. Org. Chem., 1987, vol. 52, p. 462.
Krishnamurti, R. and Henry, H.G., J. Org. Chem., 1986, vol. 51, p. 4947.
Wallace, R.H., Lu, Y., and Liu, J., Synlett, 1992, p. 992.
Rudakov, G.A., Khimiya i tekhnologiya kamfory (Chemistry and Technology of Camphor), Moscow: Lesnaya Promyshlennost’, 1976, p. 27.
Horita, N., Kamiya, Y., and Okuhara, T., Chem. Lett., 2006, vol. 35, p. 1346.
Radbil’, A.B., Zolin, B.A., Radbil’, B.A., Kulikov, M.V., and Kartashov, V.R., Russian Patent no. 2154049, 2000; Chem. Abstr., 2002, vol. 136,no. 247 716.
Pakdel, H., Sarron, S., and Roy, S.J., J. Agric. Food Chem., 2001, vol. 49, p. 4337.
Roman-Agurri, M., De la Torre-Saenz, L., Wilber, A.F., Robau-Sanchez, A., and Aguilar Elguezabal, A., Catal. Today, 2005, p. 310.
Gurvich, L.G., Zh. Fiz.-Khim. Ob-va., 1915, vol. 47, p. 827.
Rudakov, G.A., Khimiya i tekhnologiya kamfory (Chemistry and Technology of Camphor), Moscow: Lesnaya Promyshlennost’, 1976, p. 40.
Rudakov, G.A., Zh. Obshch. Khim., 1946, vol. 16, p. 261.
Volcho, K.P., Tatarova, L.E., Suslov, E.V., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Russ. J. Org. Chem., 2001, vol. 37, p. 1418.
Il’ina, I.V., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Russ. J. Org. Chem., 1999, vol. 35, p. 468.
Volcho, K.P., Tatarova, L.E., Korchagina, D.V., Salakhutdinov, N.F., Aul’chenko, I.S., Ione, K.G., and Barkhash, V.A., Zh. Org. Khim., 1994, vol. 30, p. 641.
Hamman, L.G., Meyer, J.H., Ruppar, D.A., Marschke, K.B., Lopez, F.G., Allegretto, E.A., and Karanewsky, D.S., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 1463.
Samaniego, W.N., Baldessari, A., Ponce, M.A., Rodriguez, J.B., Gros, E.G., Caram, J.A., and Marschoff, C.M., Tetrahedron Lett., 1994, vol. 35, p. 6967.
Aul’chenko, I.S., Gavrilova, T.F., Moskvichev, V.I., and Kheifits, L.A., Zh. Org. Khim., 1975, vol. 11, p. 738.
Schmidhauser, J.C., Bryant, G.L., Donahue, P.E., and Garbauskas, M.F., J. Org. Chem., 1995, vol. 60, p. 3612.
Fomenko, V.V., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Helv. Chim. Acta, 2002, vol. 85, p. 2358.
Nikitina, L.E., Startseva, V.A., Vakulenko, I.A., and Plemenkov, V.V., Russ. J. Gen. Chem., 2002, vol. 72, p. 974.
Yadav, M.K. and Jasra, R.V., Catal. Commun., 2006, vol. 7, p. 889.
Liebens, A., Mahaim, C., and Holderich, W.F., Stud. Surf. Sci. Catal., 1997, vol. 108, p. 587.
Lewis, J.B. and Hedrick, G., J. Org. Chem., 1965, vol. 30, p. 4271.
Ranu, B.C. and Jana, U., J. Org. Chem., 1998, vol. 63, p. 8212.
Carr, G., Dosanih, G., Millarand, A.P., and Whittaker, D., J. Chem. Soc., Perkin Trans. 2, 1994, p. 1419.
Ravasio, N., Finiguerra, M., and Gargano, M., Chem. Ind., 1998, vol. 75, p. 513.
Kunkeler, P.J., van der Waal, J.C., Bremmer, J., Zuurdeeg, B.J., Downing, R.S., and van Beekum, H., Catal. Lett., 1998, vol. 53, p. 135.
Polovinka, M.P., Korchagina, D.V., Gatilov, Yu.V., Vyglazov, O.G., and Barkhash, V.A., Russ. J. Org. Chem., 1999, vol. 35, p. 1292.
Motherwell, W.B., Bingham, M.J., Pothier, J., and Six, Y., Tetrahedron, 2004, vol. 60, p. 3231.
Durbetaki, A.J. and Linder, S.M., US Patent no. 2949489, 1960; Chem. Abstr., 1961, vol. 55, p. 608a–b.
Arbuzov, B.A. and Isaeva, Z.G., Zh. Obshch. Khim., 1954, vol. 24, p. 1250.
Tatarova, L.E., Korchagina, D.V., Volcho, K.P., Salakhutdinov, N.F., and Barkhash, V.A., Russ. J. Org. Chem., 2003, vol. 39, p. 1076.
Koval’skaya, S.S., Kozlova, N.G., and Shavyrin, S.V., Zh. Obshch. Khim., 1989, vol. 59, p. 1356.
Il’ina, I.V., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Russ. J. Org. Chem., 2000, vol. 36, p. 1446.
Coxon, J.M., Dansted, E., Hartshorn, M.P., and Richards, K.E., Tetrahedron, 1969, vol. 25, p. 3307.
Kergomard, A., Philibert-Bigou, J., and Geneix, M.T., Fr. Patent no. 1183849, 1959; Chem. Abstr., 1961, vol. 55, p. 144362.
Hartshorn, M.P. and Wallis, A.F.F., J. Chem. Soc. B, 1964, p. 5254.
Lopez, L., Mele, G., Fiandanese, V., Cardllicchio, C., and Nacci, A., Tetrahedron, 1994, vol. 50, p. 9097.
Il’ina, I.V., Volcho, K.P., Korchagina, D.V., Barkhash, V.A., and Salakhutdinov, N.F., Helv. Chim. Acta, 2007, vol. 90, p. 353.
Koval’skaya, S.S., Kozlov, N.G., and Kalechits, G.V., Zh. Org. Khim., 1991, vol. 27, p. 756.
Volcho, K.P., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Tetrahedron Lett., 1996, vol. 37, p. 6181.
Chapuis, C. and Brauchli, R., Helv. Chim. Acta, 1992, vol. 75, p. 1527.
Corvi Mora, C., EP Patent no. 175850, 1986; Chem. Abstr., 1986, vol. 105,no. 42384.
Il’ina, I.V., Volcho, K.P., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Russ. J. Org. Chem., 2004, vol. 40, p. 1432.
Amri, H., El Gaied, M.M., and M’Hirsi, M., J. Soc. Chim. Tunis., 1983, p. 25.
Lander, N. and Mechoulam, R., J. Chem. Soc., Perkin Trans. 1, 1976, p. 484.
Kusakari, T., Ichiyanagi, T., Kosugi, H., and Kato, M., Tetrahedron: Asymmetry, 1999, vol. 10, p. 339.
Koval’skaya, S.S. and Kozlov, N.G., Russ. J. Org. Chem., 2006, vol. 42, p. 1151.
Koval’skaya, S.S., Kozlov, N.G., and Tkachev, A.V., Russ. J. Org. Chem., 2006, vol. 42, 1141.
Il’ina, I.V., Volcho, K.P., Korchagina, D.V., Salakhutdinov, N.F., and Barkhash, V.A., Russ. J. Org. Chem., 2007, vol. 43, p. 56.
Bessiere-Chretien, Y., Montheard, J.P., El Gaied, M.M., and Bras, J.P., C.R. Acad. Sci., Ser. C, 1971, vol. 273, p. 272.
Il’ina, I.V., Volcho, K.P., Korchagina, D.V., Barkhash, V.A., and Salakhutdinov, N.F., Helv. Chim. Acta, 2006, vol. 89, p. 507.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Full Member of the Russian Academy of Sciences G.A. Tolstikov on his 75th anniversary
Original Russian Text © I.V. Il’ina, K.P. Volcho, N.F. Salakhutdinov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 1, pp. 11–31.
Irina Il’ina was born in 1975 in Mokhsogollokh village (Yakutia). In 1997 she graduated from the Novosibirsk State University (specialization organic chemistry) and in 2007 sustained her Candidate’s thesis. I. Il’ina now works as engineer at the Wood Chemistry and Natural Biologically Active Compounds Laboratory, Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences.
Field of scientific interest: chemistry of natural compounds.
Konstantin Petrovich Volcho was born in 1969 in Novosibirsk. In 1993 he graduated from the Novosibirsk State University (specialization organic chemistry) and in 1998 sustained his Candidate’s thesis in chemistry. K.P. Volcho now works as senior researcher at the Wood Chemistry and Natural Biologically Active Compounds Laboratory, Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences.
Fields of scientific interest: chemistry of natural compounds, asymmetric synthesis.
Nariman Faridovich Salakhutdinov was born in 1954 in Tashkent. In 1976 he graduated from the Samarkand State University (specialization organic chemistry). Since 1976, N.F. Salakhutdinov worked at the Novosibirsk Institute of Organic Chemistry. In 1982 he sustained his Candidate’s thesis in chemistry, and in 1998, Doctoral dissertation. N.F. Salakhutdinov is now Head of the Chemistry of Natural and Biologically Active Compounds Department at the Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences.
Fields of scientific interest: chemistry of natural and biologically active compounds.
Rights and permissions
About this article
Cite this article
Il’ina, I.V., Volcho, K.P. & Salakhutdinov, N.F. Acid-catalyzed transformations of pinane terpenoids. New prospects. Russ J Org Chem 44, 1–23 (2008). https://doi.org/10.1134/S1070428008010016
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428008010016