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Cage-like amino alcohols. synthesis, reactions, and application

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Abstract

The review analyzes methods for the synthesis of amino alcohols containing cage-like norbornene, norbornane, and adamantane fragments. Such reactions of amino alcohols as selective functionalization of hydroxy and amino groups, as well as heterocyclizations with formation of nitrogen- and oxygen-containing heterocycles, are considered. Biological activity of cage-like amino alcohols and their derivatives and their use as ligands in catalytic asymmetric syntheses are discussed.

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References

  1. Bergmeier, S.C., Tetrahedron, 2000, vol. 56, p. 2561.

    Article  CAS  Google Scholar 

  2. Lait, S.M., Rankic, D.A., and Keay, B.A., Chem. Rev., 2007, vol. 107, p. 767.

    Article  CAS  Google Scholar 

  3. Kawabata, T., Yamamoto, K., Momose, Y., Yoshida, H., Nagaoka, Y., and Fuji, K., Chem. Commun., 2001, p. 2700.

  4. Chang, J., **e, W., Wang, L., Ma, N., Cheng, S., and **e, J., Eur. J. Med. Chem., 2006, vol. 41, p. 397.

    Article  CAS  Google Scholar 

  5. Kim, D.-I., Schweri, M.M., and Deutsch, H.M., J. Med. Chem., 2003, vol. 46, p. 1456.

    Article  CAS  Google Scholar 

  6. Zou, M.-F., Kopajtic, T., Katz, J.L., and Newman, A.H., J. Med. Chem., 2003, vol. 46, p. 2908.

    Article  CAS  Google Scholar 

  7. Bois, F., Baldwin, R.M., Kula, N.S., Baldessarini, R.J., Innis, R.B., and Tamagnan, G., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 2117.

    Article  CAS  Google Scholar 

  8. Murr, B.L., Parkhill, B.J., and Nickon, A., Tetrahedron, 1992, vol. 48, p. 4845.

    Article  CAS  Google Scholar 

  9. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2002, vols. 1,2.

    Google Scholar 

  10. Shvaika, O., Osnovi sintezu likars’kikh rechovin taïkh promizhnikh produktiv (Principles of Synthesis of Medicines and Intermediate Products), Donets’k: Nord Komp’yuter, 2004.

    Google Scholar 

  11. Dryuk, V.G., Kartsev, V.G., and Voitsekhovskaya, M.A., Oksirany — sintez i biologicheskaya aktivnost’ (Oxiranes: Synthesis and Biological Activity), Moscow: Bogorodskii Pechatnik, 1999.

    Google Scholar 

  12. Kas’yan, L.I., Okovityi, S.I., and Kas’yan, A.O., Russ. J. Org. Chem., 2004, vol. 40, p. 1.

    Article  Google Scholar 

  13. Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tarabara, I.N., Alitsiklicheskie epoksidnye soedineniya. Reaktsionnaya sposobnost’ (Alicyclic Epoxy Compounds. Reactivity), Dnepropetrovsk: Dnepropetr. Nats. Univ., 2003.

    Google Scholar 

  14. Sayer, J.M., Chadha, A., Agarwal, S.K., Yeh, H.J.C., Yagi, H., and Jerina, D.M., J. Org. Chem., 1991, vol. 56, p. 20.

    Article  CAS  Google Scholar 

  15. Bazandi, K., Zaugi, R., and Blum, J., J. Heterocycl. Chem., 1996, vol. 33, p. 1703.

    Article  Google Scholar 

  16. Baertschi, S.W., Raney, K.D., Stone, M.P., and Harris, T.M., J. Am. Chem. Soc., 1988, vol. 110, p. 7929.

    Article  CAS  Google Scholar 

  17. Cristau, H.-J., Pirat, J.-L., Drag, M., and Kafarski, P., Tetrahedron Lett., 2000, vol. 41, p. 9781.

    Article  CAS  Google Scholar 

  18. Inaba, T., Yamada, Y., Sagawa, S., and Cho, H., J. Org. Chem., 2000, vol. 65, p. 1623.

    Article  CAS  Google Scholar 

  19. Bennett, F., Patel, N.M., Girijavallabhan, V.M., and Ganguly, A.K., Synlett, 1993, p. 703.

  20. Barrish, J.C., Gordon, E., Alan, M., Lin, P.-F., Bisacchi, G.S., Chen, P., Cheng, P.T.W., Fritz, A.W., Greitor, J.A., Hermsmeier, M.A., Humphreys, W.G., Lis, K.A., Marella, M.A., Merchant, Z., Mitt, T., Morrison, R.A., Obermeier, M.T., Pluscec, J., Skoog, M., Slusarchyk, W.A., Spergel, S.H., Stevenson, J.M., Sun, Ch., Sundeen, J.E., Taunk, P., Tino, J.A., Warrack, B.M., Colonno, R.J., and Zahler, R., J. Med. Chem., 1994, vol. 37, p. 1758.

    Article  CAS  Google Scholar 

  21. Harayama, T., Yanada, R., Tanaka, M., Taga, T., Machida, K., and Yoneda, F., J. Chem. Soc., Perkin Trans. 1, 1988, p. 2555.

  22. Rodriguez-Escrich, S., Popa, D., Jimeno, C., Vidal-Ferran, A., and Pericas, M.A., Org. Lett., 2005, vol. 7, p. 3829.

    Article  CAS  Google Scholar 

  23. Parker, R.E. and Isaacs, N.S., Chem. Rev., 1959, vol. 59, p. 737.

    Article  CAS  Google Scholar 

  24. Sulser, U., Widmer, J., and Goeth, H., Helv. Chim. Acta, 1977, vol. 60, p. 1676.

    Article  CAS  Google Scholar 

  25. Sabitha, G., Babu, R.S., Rajkumar, M., and Yadav, J.S., Org. Lett., 2002, vol. 4, p. 343.

    Article  CAS  Google Scholar 

  26. Okovityi, S.I., Gaponova, R.G., Platitsina, E.L., and Kas’yan, L.I., Vopr. Khim. Khim. Tekhnol., 2001, no. 2, p. 51.

    Google Scholar 

  27. Bobylev, V.A., Koldobskii, S.G., Tereshchenko, G.F., and Gidaspov, B.F., Khim. Geterotsikl. Soedin., 1998, p. 1155.

  28. Shibaev, A.Yu., Astrat’eva, N.V., and Tereshchenko, G.F., Zh. Obshch. Khim., 1984, vol. 54, p. 2744.

    CAS  Google Scholar 

  29. Omoto, K. and Fujimoto, H., J. Org. Chem., 2000, vol. 65, p. 2464.

    Article  CAS  Google Scholar 

  30. Okovityi, S.I. and Kas’yan, L.I., Visnik Dnipropetr. Univ., Khim., 2002, no. 7, p. 6.

    Google Scholar 

  31. Kas’yan, L.I., Batog, A.E., Kas’yan, A.O., Gaponova, R.G., Savel’eva, O.A., and Golodaeva, E.A., Vopr. Khim. Khim. Tekhnol., 2000, p. 34.

  32. Pantileenko, S.V., Petrov, V.V., Ratner, F.I., and Shchetinina, T.V., Russ. J. Org. Chem., 1999, vol. 35, p. 456.

    CAS  Google Scholar 

  33. Lanier, M., Le Blanc, M., and Pastor, R., Tetrahedron, 1996, vol. 52, p. 14631.

    Article  CAS  Google Scholar 

  34. Brullo, C., Bruno, O., Bondavalli, F., Schenone, S., Ranise, A., Arduino, N., Ottonello, L., and Dallegri, F., Abstracts of Papers, Joint Meeting on Medicinal Chemistry, Krakow, 2003, p. 122.

  35. Gasiorowski, K., Malinka, W., Swiatek, P., and Jaszczyszyn, A., Abstracts of Papers, Joint Meeting on Medicinal Chemistry, Krakow, 2003, p. 164.

  36. Lindström, U.M. and Somfai, P., Synthesis, 1998, p. 109.

  37. Kas’yan, L.I., Kas’yan, A.O., and Tarabara, I.N., Russ. J. Org. Chem., 2001, vol. 37, p. 1361.

    Article  Google Scholar 

  38. Lin, K.-S. and Ding, Y.-S., Bioorg. Med. Chem., 2005, vol. 13, p. 4658.

    Article  CAS  Google Scholar 

  39. Kas’yan, L.I., Kostenko, L.I., Golodaeva, E.A., Radchenko, N.D., Bondarenko, Ya.S., and Prid’ma, S.A., Vopr. Khim. Khim. Tekhnol., 2008, p. 16.

  40. Hsu, L.-F., Chang, C.-P., Li, M.C., and Chang, N.-C., J. Org. Chem., 1993, vol. 58, p. 4756.

    Article  CAS  Google Scholar 

  41. Serova, T.M., Azzheurova, I.A., and Kuznetsov, A.I., Abstracts of Papers, Mezhdunarodnaya konferentsiya “Khimiya i biologicheskaya aktivnost’ azotistykh geterotsiklov i alkaloidov” (Int. Conf. “Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and Alkaloids"), Moscow, 2001, part 2, p. 272.

  42. McKinney, M.A. and Patel, P.P., J. Org. Chem., 1973, vol. 38, p. 4059.

    Article  CAS  Google Scholar 

  43. Martinez, A.G., Vilar, E.T., Fraile, A.G., de laMoya Cerero, S., Martinez-Ruiz, P., Morillo, C.D., and Maroto, B.L., Tetrahedron Lett., 2007, vol. 48, p. 5981.

    Article  CAS  Google Scholar 

  44. Kas’yan, L.I., Russ. J. Org. Chem., 1999, vol. 35, p. 635.

    Google Scholar 

  45. Kas’yan, L.I., Zefirov, N.S., Stepanova, N.V., Saltykova, L.E., and Ryzhik, O.L., Zh. Org. Khim., 1984, vol. 20, p. 2136.

    Google Scholar 

  46. Kunz, H., Justus Liebigs Ann. Chem., 1975, p. 919.

  47. Kas’yan, L.I., Galafeeva, M.F., Kovalenko, V.V., and Dryuk, V.G., Ukr. Khim. Zh., 1987, vol. 53, p. 960.

    Google Scholar 

  48. Gaponova, R.G., Cand. Sci. (Chem.) Dissertation, Dnepropetrovsk, 1996.

  49. Michel, p. and Rassat, A., J. Org. Chem., 2000, vol. 65, p. 2572.

    Article  CAS  Google Scholar 

  50. Henkel, J.G., Faith, W.C., and Hane, J.T., J. Org. Chem., 1981, vol. 46, p. 3483.

    Article  CAS  Google Scholar 

  51. Fletcher, S.R., Baker, R., Chambers, M.S., Hobbs, S.C., and Mitchell, P.J., J. Chem. Soc., Chem. Commun., 1993, p. 1216.

  52. Cabanal-Duvillard, I., Berrien, J.-F., Ghosez, L., Husson, H.-P., and Royer, J., Tetrahedron, 2000, vol. 56, p. 3763.

    Article  CAS  Google Scholar 

  53. Golikov, A.G., Kriven’ko, A.P., and Reshetov, P.V., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2003, vol. 1, p. 65.

    Google Scholar 

  54. Khisamutdinova, R.Yu., Yarmukhamedov, N.N., Gabdrakhmanova, S.F., Karachurina, L.T., Sapozhnikova, T.A., Baibulatova, N.Z., Baschenko, N.Zh., and Zarudii, F.S., Khim.-Farm. Zh., 2004, vol. 38, no. 6, p. 27.

    Google Scholar 

  55. Afon’kin, A.A., Anikeev, A.V., Kostrikin, M.L., and Shumeiko, A.E., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2004, vol. 3, p. 511.

    Google Scholar 

  56. Welle, H.B.A. and Marko, M., US Patent no. 4406904, 1983; Chem. Abstr., 1984, vol. 100, no. 68578.

  57. Akkerman, A., van Bakel, H.C.C.K., and Smit, R.C.K., US Patent no. 4425353, 1984; Chem. Abstr., 1984, vol. 100, no. 210239.

  58. Kas’yan, L.I., Tarabara, I.N., Kas’yan, A.O., Golodaeva, E.A., and Avramenko, V.I., Visn. Dnipropetr. Univ., Khim., 2001, p. 54.

  59. Barz, M., Glas, H., and Thiel, W.R., Synthesis, 1998, p. 1269.

  60. Schenone, S., Bruno, O., Ranise, A., Bondavalli, F., Filippelli, W., Falcone, G., and Rinaldi, B., II Farmaco, 2000, vol. 55, p. 495.

    Article  CAS  Google Scholar 

  61. Schenone, S., Bruno, O., Ranise, A., Bondavalli, F., Filippelli, W., Falcone, G., and Rinaldi, B., Il Farmaco, 2000, vol. 55, p. 495.

    Article  CAS  Google Scholar 

  62. Kas’yan, L.I., Golodaeva, E.A., Kas’yan, A.O., Isaev, A.K., and Bondarenko, Ya.S., Visn. Dnipropetr. Univ., Khim., 2007, p. 48.

  63. Kas’yan, L.I., Golodaeva, E.A., Nadtoka, M.I., and Kas’yan, A.O., Visn. Dnipropetr. Univ., Khim., 2002, p. 41.

  64. Kas’yan, A.O., Golodaeva, E.A., Tsygankov, A.V., and Kas’yan, L.I., Russ. J. Org. Chem., 2002, vol. 38, p. 1606.

    Article  Google Scholar 

  65. Kas’yan, L.I., Tarabara, I.N., and Kas’yan, A.O., Russ. J. Org. Chem., 2002, vol. 38, p. 19.

    Article  Google Scholar 

  66. Kas’yan, L.I., Karpenko, D.V., Kas’yan, A.O., and Isaev, A.K., Russ. J. Org. Chem., 2005, vol. 41, p. 678.

    Article  CAS  Google Scholar 

  67. Kas’yan, L.I., Tarabara, I.N., Bondarenko, Ya.S., Shishkina, S.V., Shishkin, O.V., and Musatov, V.I., Russ. J. Org. Chem., 2005, vol. 41, p. 1122.

    Article  CAS  Google Scholar 

  68. Pal’chikov, V.A. Visn. Dnipropetr.Univ., Khim., 2008, p. 7.

  69. Kas’yan, L.I., Karat, L.D., Isaev, A.K., Prid’ma, S.A., and Kozarevich, T.A., Vopr. Khim. Khim. Tekhnol., 2007, no. 5, p. 49.

    Google Scholar 

  70. Kasyan, L.I., Pridma, S.A., Karat, L.D., Kasyan, A.O., and Isaev, A.K., Abstracts of Papers, 8th Southern School on Computational Chemistry and Materials Science, Jackson, 2008, p. 75.

  71. Kas’yan, L.I., Prid’ma, S.A., Isaev, A.K., and Karat, L.D., Abstracts of Papers, XI Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (XIth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Volgograd, 2008, p. 147.

  72. Kas’yan, L.I., Prid’ma, S.A., Turov, A.V., Pal’chikov, V.A., Kas’yan, A.O., and Karat, L.D., Russ. J. Org. Chem., 2009, vol. 45, p. 505.

    Article  CAS  Google Scholar 

  73. Kas’yan, L.I., Turov, A.V., Karat, L.D., Isaev, A.K., Golodaeva, E.A., and Prid’ma, S.A., Abstracts of Papers, XXI st Ukrains’ka konferentsiya z organichnoikhimii (XXIst Ukrainian Conf. on Organic Chemistry), Chern.g.v, 2007, p. 176.

  74. Kas’yan, A.O., Golodaeva, E.A., Yuzlenko, O.V., Shishkina, S.V., Shishkin, O.V., and Kas’yan, L.I., Russ. J. Org. Chem., 2003, vol. 39, p. 1724.

    Article  Google Scholar 

  75. Kas’yan, L.I., Golodaeva, E.A., Okovityi, S.I., Kasyan, A.O., Karpenko, D.V., and Umrykhina, L.K., Russ. J. Org. Chem., 2004, vol. 40, p. 1080.

    Article  Google Scholar 

  76. Edwards, O.E., Elder, J.W., Lesage, M., and Retallack, R.W., Can. J. Chem., 1975, vol. 53, p. 1019.

    Article  CAS  Google Scholar 

  77. Yudin, A.K., Aziridines and Epoxides in Organic Synthesis, Weinheim: Wiley-VCH, 2006.

    Book  Google Scholar 

  78. Osborn, H.M.I. and Sweeney, J., Tetrahedron: Asymmetry, 1997, vol. 8, p. 1693.

    Article  CAS  Google Scholar 

  79. Michalik, M. and Dobler, C., Tetrahedron, 1990, vol. 46, p. 7739.

    Article  CAS  Google Scholar 

  80. Koy, C., Michalik, M., Dübler, C., and Oehme, G., J. Prakt. Chem., 1997, vol. 339, p. 660.

    Article  CAS  Google Scholar 

  81. Sharpless, K.B., Chong, A.O., and Oshima, K., J. Org. Chem., 1976, vol. 41, p. 177.

    Article  CAS  Google Scholar 

  82. Bäckvall, J.E., and Björkman, E.E., J. Org. Chem., 1980, vol. 45, p. 2893.

    Article  Google Scholar 

  83. Li, G., Chang, H.-T., and Sharpless, K.B., Angew. Chem., Int. Ed. Engl., 1996, vol. 35, p. 451.

    Article  CAS  Google Scholar 

  84. Simons, S.S., J. Org. Chem., 1973, vol. 38, p. 414.

    Article  CAS  Google Scholar 

  85. Scholz, K.-H., Heine, H.-G., and Hartmann, W., Justus LiebigsAnn. Chem., 1977, p. 2027.

  86. Eissenstat, M.A. and Weaver, J.D., J. Org. Chem., 1993, vol. 58, p. 3387.

    Article  CAS  Google Scholar 

  87. Kang, S.H., Kang, S.Y., Lee, H.-S., and Buglass, A.J., Chem. Rev., 2005, vol. 105, p. 4537.

    Article  CAS  Google Scholar 

  88. Reetz, M.T., Kayser, F., and Harms, K., Tetrahedron Lett., 1992, vol. 33, p. 3458.

    Google Scholar 

  89. Stajer, G., Szabo, E.A., Fulop, F., Bernath, G., and Sohar, P., J. Heterocycl. Chem., 1983, vol. 20, p. 1181.

    Article  CAS  Google Scholar 

  90. Abstracts of Papers, XX (XXth Ukrainian Conf. on Organic Chemistry), Odessa, 2004, p. 151.

  91. Alves, M.J., Garcia-Mera, X., Vale, M.L.C., Santos, T.P., Aguiar, F.R., and Rodriguez-Borges, J.E., Tetrahedron Lett., 2006, vol. 47, p. 7595.

    Article  CAS  Google Scholar 

  92. Davies, R.G., Gibson, V.C., Hursthouse, M.B., Light, M.E., Marshall, E.L., North, M., Robson, D.A., Thompson, J., White, J.P., Williams, D.J, and Williams, P.J., J. Chem. Soc., Perkin Trans. 1, 2001, p. 3365.

  93. Martins, J.E.D., Mehlecke, C.M., Gamba, M., and Costa, V.E.U., Tetrahedron: Asymmetry, 2006, vol. 17, p. 1817.

    Article  CAS  Google Scholar 

  94. Tolstikov, G.A., Dembitskii, V.M., Tolstikova, T.G., and Shul’ts, E.E., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2003, vol. 1, p. 418.

    CAS  Google Scholar 

  95. Olivo, H.F., Hemenway, M.S., and Gezginci, M.H., Tetrahedron Lett., 1998, vol. 39, p. 1309.

    Article  CAS  Google Scholar 

  96. Olivo, H.F. and Hemenway, M.S., J. Org. Chem., 1999, vol. 64, p. 8968.

    Article  CAS  Google Scholar 

  97. Alvarez, C., Pelaez, R., and Medarde, M., Tetrahedron, 2007, vol. 63, p. 2132.

    Article  CAS  Google Scholar 

  98. Mino, T., Hata, S., Ohtaka, K., Sakamoto, M., and Fujita, T., Tetrahedron Lett., 2001, vol. 42, p. 4837.

    Article  CAS  Google Scholar 

  99. Hari, Y. and Aoyama, T., Synthesis, 2005, p. 583.

  100. Hanyu, N., Mino, T., Sakamoto, M., and Fujita, T., Tetrahedron Lett., 2000, vol. 41, p. 4587.

    Article  CAS  Google Scholar 

  101. Balsamo, A., Breschi, M.C., Lapucci, A., Macchia, B., Macchia, F., Martinotti, E., Nencetti, S., Nieri, P., and Orlandini, E., J. Med. Chem., 1989, vol. 32, p. 856.

    Article  CAS  Google Scholar 

  102. Morrow, D.F., Johnson, P.C., Torabi, H., Williams, D., Wedding, D.L., Craig, J.W., Majewski, R.F., Braselton, J.P., and Gallo, D.G., J. Med. Chem., 1973, vol. 16, p. 736.

    Article  CAS  Google Scholar 

  103. Davis, D.P., Borchardt, R.T., and Grunewald, G.L., J. Med. Chem., 1981, vol. 24, p. 12.

    Article  CAS  Google Scholar 

  104. Olsson, C., Helgesson, S., and Frejd, T., Tetrahedron: Asymmetry, 2008, vol. 19, p. 1484.

    Article  CAS  Google Scholar 

  105. Kadutskii, A.P., Kozlov, N.G., Kuchin, A.V., and Frolova, L.L., Abstracts of Papers, XI Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (XIth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Volgograd, 2008, p. 112.

  106. Patrusheva, O.V., Akimova, T.I., and Vysotskii, V.I., Abstracts of Papers, X Mezhdunarodnaya nauchnotekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (Xth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Samara, 2004, p. 200.

  107. De Oliveira, L.F. and Costa, V.E.U., Tetrahedron: Asymmetry, 2004, vol. 15, p. 2583.

    Article  CAS  Google Scholar 

  108. Markowicz, S.W., Pokrzeptowicz, K., Karolak-Wojciechowska, J., Czylkowski, R., Omelanczuk, J., and Sobczak, A., Tetrahedron: Asymmetry, 2002, vol. 13, p. 1981.

    Article  CAS  Google Scholar 

  109. Katoh, T., Izuhara, T., Yokota, W., Inoue, M., Watanabe, K., Nobeyama, A., and Suzuki, T., Tetrahedron, 2006, vol. 62, p. 1590.

    Article  CAS  Google Scholar 

  110. Ager, D.J., Prakash, I., and Schaad, D.R., Chem. Rev., 1996, vol. 96, p. 835.

    Article  CAS  Google Scholar 

  111. Ager, D.J., Prakash, I., and Schaad, D.R., Aldrichim. Acta, 1997, vol. 30, p. 3.

    CAS  Google Scholar 

  112. Eguchi, S., Furukawa, Y., Suzuki, T., Kondo, K., and Sasaki, T., J. Org. Chem., 1985, vol. 50, p. 1895.

    Article  CAS  Google Scholar 

  113. Seebacher, W., Berger, H., Kaiser, M., Brun, R., Saf, R., and Weis, R., Monatsh. Chem., 2006, vol. 137, p. 471.

    Article  CAS  Google Scholar 

  114. Kas’yan, L.I., Golodaeva, E.A., Kas’yan, A.O., and Isaev, A.K., Russ. J. Org. Chem., 2003, vol. 39, p. 1398.

    Article  Google Scholar 

  115. **, C., Burgess, J.P., Rehder, K.S., and Brine, G.A., Synthesis, 2007, p. 219.

  116. Thanh, G.V., Pegot, B., and Loupy, A., Eur. J. Org. Chem., 2004, p. 1112.

  117. Adam, W., Roschmann, K.J., and Saha-Möller, C.R., Eur. J. Org. Chem., 2000, p. 557.

  118. Kasyan, L.I., Sereda, S.V., Potekhin, K.A., and Kasyan, A.O., Heteroatom Chem., 1997, vol. 8, p. 177.

    Article  CAS  Google Scholar 

  119. Earley, W.G., Jacobsen, L.E., Madin, A., Meier, G.P., O’Donnell, C.J., Oh, T., Old, D.W., Overman, L.E., and Sharp, M.J., J. Am. Chem. Soc., 2005, vol. 127, p. 18046.

    Article  CAS  Google Scholar 

  120. Martinez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., Martinez-Ruiz, P., and Morillo, C.D., Tetrahedron: Asymmetry, 2007, vol. 18, p. 742.

    Article  CAS  Google Scholar 

  121. Li, X., Lou, R., Yeung, C.-H., Chan, A.S.C., and Wong, W.K., Tetrahedron: Asymmetry, 2000, vol. 11, p. 2077.

    Article  CAS  Google Scholar 

  122. Seebacher, W., Schlapper, C., Brun, R., Kaiser, M., Saf, R., and Weis, R., Eur. J. Med. Chem., 2006, vol. 41, p. 970.

    Article  CAS  Google Scholar 

  123. Seebacher, W., Brun, R., Kaiser, M., Saf, R., and Weis, R., Eur. J. Med. Chem., 2005, vol. 40, p. 888.

    Article  CAS  Google Scholar 

  124. Schlapper, C., Seebacher, W., Kaiser, M., Brun, R., Saf, R., and Weis, R., Eur. J. Med. Chem., 2008, vol. 43, p. 800.

    Article  CAS  Google Scholar 

  125. Birgele, I.S., Kemme, A.A., and Kupge, E.L., Kremniiorganicheskie proizvodnye aminospirtov: fiziko-khimicheskie issledovaniya (Organosilicon Derivatives of Amino Alcohols: Physicochemical Studies), Riga: Zinatne, 1987.

    Google Scholar 

  126. Glushko, L.P. and Petukhova, E.I., Pridnipr. Nauk. Visn., Khim., 1998, p. 60.

  127. Evans, P.A., Nelson, J.D., and Rheingold, A.L., Tetrahedron Lett., 1997, vol. 38, p. 2235.

    Article  CAS  Google Scholar 

  128. Fulop, F., Stajer, G., Bernath, G., and Sohar, P., Magy. Kem. Foly., 1986, vol. 92, p. 86.

    CAS  Google Scholar 

  129. Golodaeva, E.A., Cand. Sci. (Chem.) Dissertation, Dnepropetrovsk, 2002.

  130. Davies, S.R., Cain, C.P., Glossop, M.T., Mengent, M.-L., and Kee, T.P., Synth. Commun., 2004, vol. 34, p. 1191.

    Article  CAS  Google Scholar 

  131. Roth, G.P., Leonard, S.F., and Tong, L., J. Org. Chem., 1996, vol. 61, p. 5710.

    Article  CAS  Google Scholar 

  132. Stajer, G., Mod, L., Szabo, A.E., Fulop, F., and Bernath, G., Tetrahedron, 1984, vol. 40, p. 2385.

    Article  CAS  Google Scholar 

  133. Collon, S., Kouklovsky, C., and Langlois, Y., Eur. J. Org. Chem., 2002, p. 3566.

  134. Yamakuchi, M., Matsunaga, H., Tokuda, R., Ishizuka, T., Nakajima, M., and Kunieda, T., Tetrahedron Lett., 2005, vol. 46, p. 4019.

    Article  CAS  Google Scholar 

  135. Ahn, K.H., Lee, S., and Lim, A., J. Org. Chem., 1992, vol. 57, p. 5065.

    Article  CAS  Google Scholar 

  136. Ahn, K.H., Lim, A., and Lee, S., Tetrahedron: Asymmetry, 1993, vol. 4, p. 2435.

    Article  CAS  Google Scholar 

  137. Morozov, I.S., Petrov, V.I., and Sergeeva, S.A., Farmakologiya adamantanov (Pharmacology of Adamantanes), Volgograd: Volgogr. Med. Akad., 2001.

    Google Scholar 

  138. Bagrii, E.I. and Saginaev, A.T., Usp. Khim., 1983, vol. 52, p. 1538.

    CAS  Google Scholar 

  139. Indulen, M.K., Kalninya, V.A., Ryazantseva, G.M., and Bubovich, V.I., Mekhanizmy antivirusnogo deistviya proizvodnykh adamantana (Mechanisms of Antiviral Action of Adamantane Derivatives), Riga: Zinatne, 1981.

    Google Scholar 

  140. Bagrii, E.I., Adamantany: poluchenie, svoistva, primenenie (Adamantanes: Synthesis, Properties, and Application), Moscow: Nauka, 1989.

    Google Scholar 

  141. Leneva, I.A., Glushkov, R.G., and Gus’kova, T.A., Khim.-Farm. Zh., 2004, vol. 38, p. 8.

    Google Scholar 

  142. Klimochkin, Yu.N., Moiseev, I.K., Abramov, O.V., Vladyko, G.V., Korobchenko, L.V., and Boreko, E.I., Khim.-Farm. Zh., 1991, vol. 25, p. 49.

    CAS  Google Scholar 

  143. Kiseleva, Ya.Yu., Perminova, N.G., Plyasunova, O.A., Timofeev, D.I., Serbin, A.V., Kas’yan, L.I., Egorov, Yu.A., Grebinik, T.S., and Timofeev, I.V., Molek. Genet., Epidemiol. Virusol., 2005, p. 33.

  144. Danilenko, G.I., Shablovskaya, E.A., Antonova, L.I., Guzhova, S.V., Lobanova, I.A., Dyachenko, A.P., and Panasyuk, A.I., Khim.-Farm. Zh., 1998, vol. 32, no. 2, p. 28.

    CAS  Google Scholar 

  145. Scholtissek, C., Quack, G., Klenk, H.D., and Webster, R.G., Antiviral Res., 1998, vol. 37, p. 83.

    Article  CAS  Google Scholar 

  146. Golovin, E.V., Golovina, O.V., Guseva, G., Shiryaev, A.K., and Klimochkin, Yu.N., Abstracts of Papers, X Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (Xth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Samara, 2004, p. 110.

  147. Clariana, J., Garcia-Granda, S., Gotor, V., GutierrezFernandez, A., Luna, A., Moreno-Manas, M., and Vallribera, A., Tetrahedron: Asymmetry, 2000, vol. 11, p. 4549.

    Article  CAS  Google Scholar 

  148. Plakhotnik, V.M., Kovtun, V.Yu., Krasutskii, P.A., Novikova, M.I., Prokhorov, A.B., Yurchenko, A.G., and Yashunskii, V.G., Zh. Org. Khim., 1981, vol. 17, p. 1447.

    CAS  Google Scholar 

  149. Krasuskii, P.A., Semenova, I.G., Novikova, M.I., Yurchenko, A.G., Leont’eva, N.A., and Veselovskaya, T.V., Khim.-Farm. Zh., 1987, vol. 21, p. 836.

    Google Scholar 

  150. Augeri, D.J., Robl, J.A., Betebenner, D.A., Magnin, D.R., Khanna, A., Robertson, J.G., Wang, A., Simpkins, L.M., Taunk, P., Huang, Q., Han, S.-P., Abboa-Offei, B., Cap, M., **n, L., Tao, L., Tozzo, E., Welzel, G.E., Egan, D.M., Marcinkeviciene, J., Chang, S.Y., Biller, S.A., Kirby, V.S., Parker, R.A., and Hamann, L.G., J. Med. Chem., 2005, vol. 48, p. 5025.

    Article  CAS  Google Scholar 

  151. Jaroskova, L., van der Veken, L., de Belser, P., Diels, G., de Groot, A., and Linders, J.T.M., Tetrahedron Lett., 2006, vol. 47, p. 8063.

    Article  CAS  Google Scholar 

  152. Mukhametshina, L.F., Shchadneva, N.A., Khusnutdinov, R.I., and Dzhemilev, U.M., Abstracts of Papers, XI Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (XIth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Volgograd, 2008, p. 79.

  153. Kuznetsov, S.A. and Klimochkin, Yu.N., Abstracts of Papers, XI Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (XIth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Volgograd, 2008, p. 187.

  154. Butov, G.M., Mokhov, V.M., and Kunaev, R.U., Abstracts of Papers, X Mezhdunarodnaya nauchnotekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (Xth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Samara, 2004, p. 82.

  155. Shiryaev, A.K., Moiseev, I.K., Boreko, E.I., Korobchenko, L.V., and Vladyko, G.V., Khim.-Farm. Zh., 1990, vol. 24, no. 5, p. 23.

    CAS  Google Scholar 

  156. Polis, Ya.Yu. and Vilne, B.Yu., USSR Inventor’s Certificate no. 368236, 1973; Ref. Zh., Khim., 1973, no. 22N302P.

  157. Kas’yan, L.I., Kas’yan, A.O., and Golodaeva, E.A., Russ. J. Org. Chem., 2000, vol. 36, p. 1722.

    Google Scholar 

  158. Kas’yan, L.I., Golodaeva, E.A., Tarabara, I.N., and Kas’yan, A.O., Abstracts of Papers, I Vserossiiskaya konferentsiya po khimii geterotsiklov pamyati A.N. Kosta (Ist All-Russian Conf. on the Chemistry of Heterocycles in Memory of A.N. Kost), Suzdal’, 2000, p. 204.

  159. Kas’yan, L.I., Golodaeva, E.A., and Kas’yan, A.O., Russ. J. Org. Chem., 2003, vol. 39, p. 1248.

    Article  Google Scholar 

  160. Clariana, J., Comelles, J., Moreno-Manas, M., and Vallribera, A., Tetrahedron: Asymmetry, 2002, vol. 13, p. 1551.

    Article  CAS  Google Scholar 

  161. Zefirova, O.N., Nurieva, E.V., Nuriev, V.N., Zyk, N.V., and Zefirov, N.S., XI Mezhdunarodnaya nauchnotekhnicheskaya konferentsiya “Perspektivy razvitiya khimii i prakticheskogo primeneniya alitsiklicheskikh soedinenii” (XIth Int. Scientific and Technical Conf. “Prospects in the Development of Chemistry and Practical Application of Alicyclic Compounds"), Volgograd, 2008, p. 124.

  162. Lieb, F., Oediger, H., Böshagen, H., Rosentreter, U., Niewöhner, U., Hoever, P., Perzborn, E., Seuter, F., and Fiedler, V.-B., FRG Patent Appl. no. 3720760, 1989; Ref. Zh., Khim., 1990, no. 2O80P.

  163. Hamanaka, N., Seko, T., Miyazaki, T., and Naka, M., Tetrahedron Lett., 1989, vol. 30, p. 2399.

    Article  CAS  Google Scholar 

  164. Ohtani, M. and Narisada, M., J. Med. Chem., 1990, vol. 33, p. 1027.

    Article  CAS  Google Scholar 

  165. Murata, M., Ikoma, S., and Achiwa, K., Chem. Pharm. Bull., 1990, vol. 38, p. 2329.

    CAS  Google Scholar 

  166. Zlenko, O.T., Mamchur, V.I., Kas’yan, L.I., Golodaeva, O.A., Slesarchuk, V.Yu., Makarenko, O.V., and Krishchik, O.V., (IXth Congr. of World Federation of Ukrainian Medical Societies), Lugans’k, 2002, p. 460.

  167. Zlenko, O.T., Mamchur, V.I., Oprishko, V.I., Kasyan, L.I., Kas’yan, A.O., Golodaeva, O.A., and Zarovna, I.S., Ukr. Med. Visti, 2003, vol. 5, p. 210.

    Google Scholar 

  168. Zlenko, H.T., Mamchur, V.I., Skachko, T.A., Kasyan, L.I., Kasyan, A.O., Pridma, S.A., and Palchikov, V.A., Abstracts of Papers, DGPPN Congress 2006, Berlin, 2006, p. 131.

  169. Kasyan, L.I., Golodayeva, E.A., Zlenko, E.T, and Seferova, M.F., Abstracts of Papers, Int. Conf. on the Chemistry of Nitrogen-Containing Heterocycles, Kharkiv, 2006, p. 242.

  170. Mamchur, V.I., Kas’yan, L.I., Zlenko, O.T., Kas’yan, A.O., Golodaeva, O.A., Seferova, M.F., Prishlyak, I.S., and Oprishko, V.I., Ukrainian Patent no. 81 502, 2008.

  171. Kasyan, L.I., Zlenko, H.T., Golodayeva, H.A., Kasyan, A.O., and Karpenko, D.V., Abstracts of Papers, Joint Meeting on Medicinal Chemistry, Krakow, 2003, p. 139.

  172. Pupi, A., Berti, G., and Bottoncetti, A., EPV Patent no. 0972764, 2000; Ref. Zh., Khim., 2000, no. 19O126P.

  173. Zhang, Y., Rothman, R.B., Dersch, C.M., de Costa, B.R., Jacobson, A.E., and Rice, K.C., J. Med. Chem., 2000, vol. 43, p. 4840.

    Article  CAS  Google Scholar 

  174. Loriga, G., Ruiu, S., Manca, I., Murineddu, G., Dessi, C., Pani, L., and Panna, G.A., Bioorg. Med. Chem., 2007, vol. 15, p. 3748.

    Article  CAS  Google Scholar 

  175. Brown, A.D., Bunnage, M.E., Glossop, P.A., James, K., Jones, R., Lane, S.A.L., Lewthwaite, R.A., Mantell, S., Perros-Huguet, C., Price, D.A., Trevethick, M., and Webster, R., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 1280.

    Article  CAS  Google Scholar 

  176. Brown, A.D., Bunnage, M.E., Glossop, P.A., James, K., Jones, R., Lane, S.A.L., Lewthwaite, R.A., Mantell, S., Perros-Huguet, C., Price, D.A., Trevethick, M., and Webster, R., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 4012.

    Article  CAS  Google Scholar 

  177. Ovchinnikov, K.A., Pozdnyakov, V.V., and Moiseev, I.K., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 2005, vol. 48, p. 71.

    CAS  Google Scholar 

  178. Lv, J., Qian, Y., Liu, T., and Wang, Y., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 4102.

    Article  CAS  Google Scholar 

  179. Weis, R., Kaiser, M., Brun, R., Saf, R., and Seebacher, W., Monatsh. Chem., 2006, vol. 137, p. 1365.

    Article  CAS  Google Scholar 

  180. Schlapper, C., Seebacher, W., Kaiser, M., Brun, R., Saf, R., and Weis, R., Bioorg. Med. Chem., 2007, vol. 15, p. 5543.

    Article  CAS  Google Scholar 

  181. Noyori, R. and Kitamura, M., Angew. Chem., Int. Ed. Engl., 1991, vol. 30, p. 49.

    Article  Google Scholar 

  182. Noyori, R., Angew. Chem., Int. Ed., 2002, vol. 41, p. 2008.

    Article  CAS  Google Scholar 

  183. Cardillo, G. and Orena, M., Tetrahedron, 1990, vol. 46, p. 3321.

    Article  CAS  Google Scholar 

  184. Grajewska, A. and Rozwadowska, M.D., Tetrahedron: Asymmetry, 2007, vol. 18, p. 803.

    Article  CAS  Google Scholar 

  185. Kizirian, J.-C., Chem. Rev., 2008, vol. 108, p. 140.

    Article  CAS  Google Scholar 

  186. Castellnou, D., Sola, L., Jimeno, C., Fraile, J.M., Mayoral, J.A., Riera, A., and Pericas, M.A., J. Org. Chem., 2005, vol. 70, p. 433.

    Article  CAS  Google Scholar 

  187. Blaser, H.-U., Chem. Rev., 1992, vol. 92, p. 935.

    Article  CAS  Google Scholar 

  188. Kitamura, M., Suga, S., Kawai, K., and Noyori, R., J. Am. Chem. Soc., 1986, vol. 108, p. 6071.

    Article  CAS  Google Scholar 

  189. Jimeno, C., Pasto, M., Riera, A., and Pericas, M.A., J. Org. Chem., 2003, vol. 68, p. 3130.

    Article  CAS  Google Scholar 

  190. Cho, B.T. and Kim, N., J. Chem. Soc., Perkin Trans. 1, 1996, p. 2901.

  191. Paleo, M.R., Cabeza, I., and Sardina, F.J., J. Org. Chem., 2000, vol. 65, p. 2108.

    Article  CAS  Google Scholar 

  192. Hayashi, M., Kaneko, T., and Oguni, N., J. Chem. Soc., Perkin Trans. 1, 1991, p. 25.

  193. El-Shehawy, A.A., Abdelaal, M.Y., Watanabe, K., Ito, K., and Itsuno, S., Tetrahedron: Asymmetry, 1997, vol. 8, p. 1731.

    Article  CAS  Google Scholar 

  194. Hartikka, A., Modin, S.A., Andersson, P.G., and Arvidsson, P.I., Org. Biomol. Chem., 2003, vol. 1, p. 2522.

    Article  CAS  Google Scholar 

  195. Haddad, T.D., Hirayama, L.C., Taynton, P., and Singaram, B., Tetrahedron Lett., 2008, vol. 49, p. 508.

    Article  CAS  Google Scholar 

  196. Wang, Y., Liu, X., and Deng, L., J. Am. Chem. Soc., 2006, vol. 128, p. 3928.

    Article  CAS  Google Scholar 

  197. Roth, P., Andersson, P.G., and Somfai, P., Chem. Commun., 2002, p. 1752.

  198. Kloetzing, R.J., Thaler, T., and Knochel, P., Org. Lett., 2006, vol. 8, p. 1125.

    Article  CAS  Google Scholar 

  199. Jeon, S.-J., Chen, Y.K., and Walsh, P.J., Org. Lett., 2005, vol. 7, p. 1729.

    Article  CAS  Google Scholar 

  200. Chen, Y.-J., Lin, R.-X., and Chen, C., Tetrahedron: Asymmetry, 2004, vol. 15, p. 3561.

    Article  CAS  Google Scholar 

  201. Chen, Y.-J., Lee, P.T., and Chen, C., Tetrahedron: Asymmetry, 2005, vol. 16, p. 2704.

    Article  CAS  Google Scholar 

  202. Markovicz, S.W., Figlus, M., Legkovwski, M., Karolak-Wogciechowska, J., Dzierzawska-Magewska, A., and Verpoort, F., Tetrahedron: Asymmetry, 2006, vol. 17, p. 434.

    Article  CAS  Google Scholar 

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Original Russian Text © L.I. Kas’yan, V.A. Pal’chikov, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 1, pp. 7–43.

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Kas’yan, L.I., Pal’chikov, V.A. Cage-like amino alcohols. synthesis, reactions, and application. Russ J Org Chem 46, 1–42 (2010). https://doi.org/10.1134/S107042801001001X

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