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Ozonolysis of Unsaturated Compounds in the Synthesis of Insect Pheromones and Juvenoids

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Chemistry of Natural Compounds Aims and scope

Research from the last 20 years on the use of ozonolysis of cyclic and acyclic mono- and dienes and aromatic compounds in various steps of the total synthesis of insect pheromones and juvenoids was reviewed.

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References

  1. V. V. Plemenkov, Chemistry of Isoprenoids [in Russian], Izd. Altaiskogo Univ., Kaliningrad, Kazan, Barnaul, 2007, 322 pp.

  2. M. Jacobson, Insect Sex Pheromones, Academic Press, New York, 1972.

    Google Scholar 

  3. K. V. Lebedeva, V. A. Minyailo, and Yu. B. Pyatnova, Insect Pheromones [in Russian], Nauka, Moscow, 1984, 268 pp.

    Google Scholar 

  4. Yu. A. Ovchinnikov, Bioorganic Chemistry [in Russian], Prosveshchenie, Moscow, 1987, 815 pp.

    Google Scholar 

  5. V. N. Odinokov and E. P. Serebryakov, Synthesis of Insect Pheromones [in Russian], Gilem, Ufa, 2001, 372 pp.

  6. V. N. Odinokov, V. N. Burov, and O. S. Kukovinets, Semiochemicals in the Protection of Grain and Grain Products from Harmful Insects [in Russian], Gilem, Ufa, 2005, 232 pp.

  7. T. I. Zvereva, V. G. Kasradze, O. B. Kazakova, and O. S. Kukovinets, Zh. Org. Khim., 46, 1431 (2010).

    CAS  Google Scholar 

  8. G. Yu. Ishmuratov, Yu. V. Legostaeva, L. P. Botsman, and G. A. Tolstikov, Zh. Org. Khim., 46, 1591 (2010).

    Google Scholar 

  9. V. N. Odinokov, Mendeleev Commun., 217 (2005).

  10. G. Yu. Ishmuratov, R. Ya. Kharisov, V. N. Odinokov, and G. A. Tolstikov, Usp. Khim., 63, 580 (1994).

    Google Scholar 

  11. V. N. Odinokov, L. P. Botsman, and E. V. Gladysheva, Chem. Nat. Compd., 32, 381 (1996).

    Article  Google Scholar 

  12. A. G. Kukovinets, T. A. Kargapol’tseva, O. S. Kukovinets, F. Z. Galin, V. V. Zorin, F. A. Shakhova, and G. A. Tolstikov, Zh. Org. Khim., 36, 237 (2000).

    Google Scholar 

  13. N. A. Plate and E. V. Slivinskii, Principles of Monomer Chemistry and Technology: Student Aide [in Russian], Nauka: MAIK Nauka/Interperiodika, Moscow, 2002, 696 pp.

    Google Scholar 

  14. T. I. Zvereva, O. S. Kukovinets, V. G. Kasradze, M. I. Abdullin, and F. Z. Galin, Bashk. Khim. Zh., 14, 30 (2007).

    CAS  Google Scholar 

  15. O. S. Kukovinets, V. G. Kasradze, E. V. Chernukha, V. N. Odinokov, A. V. Dolidze, F. Z. Galin, L. V. Spirikhin, M. I. Abdullin, and G. A. Tolstikov, Zh. Org. Khim., 35, 1185 (1999).

    Google Scholar 

  16. O. S. Kukovinets, V. G. Kasradze, E. V. Chernukha, V. N. Odinokov, F. Z. Galin, M. I. Abdullin, P. I. Fedorov, and G. A. Tolstikov, Zh. Org. Khim., 36, 234 (2000).

    Google Scholar 

  17. O. S. Kukovinets, V. G. Kasradze, E. V. Salimova, V. N. Odinokov, F. Z. Galin, and P. I. Fedorov, Chem. Nat. Compd., 35, 358 (1999).

    Article  CAS  Google Scholar 

  18. G. Yu. Ishmuratov, R. Ya. Kharisov, and I. M. Muslimova, in: Proceedings of the 2nd All-Russian Convention “Wood Chemistry and Organic Synthesis” [in Russian], Syktyvkar, 1996, p. 24.

  19. V. N. Odinokov, V. R. Akhmetova, and R. G. Savchenko, Chem. Nat. Compd., 34, 96 (1998).

    Article  CAS  Google Scholar 

  20. V. N. Odinokov, V. R. Akhmetova, G. Yu. Ishmuratov, L. P. Botsman, and G. A. Tolstikov, Zh. Org. Khim., 22, 953 (1986).

    CAS  Google Scholar 

  21. V. N. Odinokov, O. S. Kukovinets, R. A. Zainullin, V. G. Kasradze, A. V. Dolidze, and G. A. Tolstikov, Zh. Org. Khim., 28, 1178 (1992).

    CAS  Google Scholar 

  22. V. G. Kasradze, Candidate Dissertation, Inst. Org. Chem., Ufa Sci. Cent., RAS, Ufa, 1994, 21 pp.

  23. O. S. Kukovinets, V. G. Kasradze, V. N. Odinokov, L. V. Spirikhin, and G. A. Tolstikov, in: Proceedings of the 2nd All-Russian Convention “Wood Chemistry and Organic Synthesis” [in Russian], Syktyvkar, 1996, p. 25.

  24. G. Yu. Ishmuratov, R. Ya. Kharisov, O. V. Botsman, V. V. Zorin, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1929 (2000).

  25. V. N. Odinokov, O. S. Kukovinets, V. G. Kasradze, A. V. Dolidze, V. R. Akhmetova, E. P. Serebryakov, and G. A. Tolstikov, Zh. Org. Khim., 29, 39 (1993).

    CAS  Google Scholar 

  26. O. S. Kukovinets, V. G. Kasradze, V. N. Odinokov, and G. A. Tolstikov, Khim. Interesakh Ustoich. Razvit., 20, 1 (2012).

    Google Scholar 

  27. O. Irie and K. Shishido, Chem. Lett., 53 (1995).

  28. M. I. Goryaev, Characteristics of Chemical Compounds in Essential Oils [in Russian], Izd. Akad. Nauk Kaz. SSR, Alma-Ata, 1953, 371 pp.

  29. K. Mori and Y. Nakazono, Tetrahedron, 42, 283 (1986).

    Article  CAS  Google Scholar 

  30. K. Tadano, Y. Isshiki, M. Minami, and S. Ogawa, J. Org. Chem., 58, 6266 (1993).

    Article  CAS  Google Scholar 

  31. O. S. Kukovinets, M. I. Kislitsyn, R. A. Zainullin, M. I. Abdullin, and F. Z. Galin, Russ. J. Org. Chem., 42, 396 (2006).

    Article  CAS  Google Scholar 

  32. M. I. Kislitsyn, R. V. Kunakova, and R. A. Zainullin, in: Proceedings of the Republic Scientific-Practical Conference of Young Scientists “Young Scientists of the New Millennium [in Russian], Ufa, 2000, p. 150.

  33. E. A. Lozhkina, Candidate Dissertation, Inst. Org. Chem., Ufa Sci. Cent., RAS, Ufa, 1995, 16 pp.

  34. G. A. Tolstikov, V. N. Odinokov, O. S. Kukovinets, V. Zh. Bikulova, E. A. Lozhkina, G. Yu. Ishmuratov, N. V. Volchkov, and O. M. Nefedov, SU Pat. No. 1,671,657, Aug. 23, 1991; Byull. Izobret., No. 31, 2 (1991).

  35. N. Y. Grigorieva and P. G. Tsiklauri, Russ. Chem. Rev., 69, 573 (2000).

    Article  CAS  Google Scholar 

  36. G. Yu. Ishmuratov, L. P. Botsman, and Yu. V. Legostaeva, in: Proceedings of the All-Russian Scientific Conference “Biostimulators in Medicine and Agriculture” Dedicated to the 10th Anniversary of the Department of Bioorganic Chemistry of Bashkir State Univ., Ufa, RITs BashGU, 2011, p. 58.

  37. V. N. Odinokov, O. S. Kukovinets, R. A. Zainullin, V. G. Kasradze, and G. A. Tolstikov, Zh. Org. Khim., 31, 103 (1995).

    CAS  Google Scholar 

  38. R. P. van Summeren, S. J. W. Reijmer, B. L. Feringa, and A. J. Minnaard, Chem. Commun., 1387 (2005).

  39. E. C. Wayne, C. W. Jerome, and M. M. Vasilios, Tetrahedron Lett., 47, 2217 (2006).

    Article  Google Scholar 

  40. G. Yu. Ishmuratov, R. Ya. Kharisov, M. P. Yakovleva, O. V. Botsman, R. R. Muslukhov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 198 (1999).

  41. G. Yu. Ishmuratov, R. Ya. Kharisov, M. P. Yakovleva, O. V. Botsman, R. R. Muslukhov, and G. A. Tolstikov, Zh. Org. Khim., 37, 49 (2001).

    Google Scholar 

  42. F.-C. Liu, W.-X. Li, Y.-C. Wang, and J. Lin, Synth. Commun., 25, 3837 (1995).

    Article  CAS  Google Scholar 

  43. O. S. Kukovinets, T. I. Zvereva, V. G. Kasradze, F. Z. Galin, L. L. Frolova, A. V. Kuchin, L. V. Spirikhin, and M. I. Abdullin, Chem. Nat. Compd., 42, 216 (2006).

    Article  CAS  Google Scholar 

  44. A. M. Kim, Organic Chemistry: Student Aide for Higher Educational Institutions [in Russian], Sib. Univ. Izd., Novosibirsk, 2004, 844 pp.

    Google Scholar 

  45. G. Yu. Ishmuratov, M. P. Yakovleva, G. V. Zaripova, L. P. Botsman, R. R. Muslukhov, and G. A. Tolstikov, Chem. Nat. Compd., 40, 548 (2004).

    Article  CAS  Google Scholar 

  46. A. M. Moiseenkov and B. A. Cheskis, Dokl. Akad. Nauk SSSR, 290, 1379 (1986).

    CAS  Google Scholar 

  47. B. A. Cheskis and A. M. Moiseenkov, Khim.-farm. Zh., 22, 597 (1988).

    Google Scholar 

  48. G. Yu. Ishmuratov, R. Ya. Kharisov, R. R. Gazetdinov, and G. A. Tolstikov, Chem. Nat. Compd., 41, 617 (2005).

    Article  CAS  Google Scholar 

  49. G. Yu. Ishmuratov, R. Ya. Kharisov, E. R. Latypova, and R. F. Talipov, Chem. Nat. Compd., 42, 367 (2006).

    Article  CAS  Google Scholar 

  50. R. R. Gazetdinov, Candidate Dissertation, Inst. Org. Chem., Ufa Sci. Cent., RAS, Ufa, 2004, 100 pp.

  51. V. N. Odinokov, L. P. Botsman, and G. A. Emel’yanova, Russ. Chem. Bull. Int. Ed., 47, 2021 (1998).

    Article  CAS  Google Scholar 

  52. R. Ya. Kharisov, R. R. Gazetdinov, O. V. Botsman, R. R. Muslukhov, G. Yu. Ishmuratov, and G. A. Tolstikov, Zh. Org. Khim., 38, 1047 (2002).

    Google Scholar 

  53. R. Ya. Kharisov, O. V. Botsman, R. R. Gazetdinov, G. Yu. Ishmuratov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1067 (2001).

  54. R. R. Gazetdinov, R. Ya. Kharisov, V. V. Zorin, and G. Yu. Ishmuratov, Bashk. Khim. Zh., 10, 37 (2003).

    Google Scholar 

  55. G. Yu. Ishmuratov, R. Ya. Kharisov, R. R. Gazetdinov, and V. V. Zorin, Bashk. Khim. Zh., 11, 39 (2004).

    CAS  Google Scholar 

  56. G. Yu. Ishmuratov, V. S. Tukhvatshin, and R. F. Talipov, Butlerov. Soobshch., 36, 69 (2013).

    Google Scholar 

  57. G. Yu. Ishmuratov, A. V. Bannova, E. R. Latypova, V. S. Tukhvatshin, O. S. Kukovinets, R. R. Muslukhov, and G. A. Tolstikov, Zh. Org. Khim., 49, 52 (2013).

    Google Scholar 

  58. W. Treibs and H. Albrecht, J. Prakt. Chem., 13, 291 (1961).

    Article  CAS  Google Scholar 

  59. G. V. Kryshtal’, G. M. Zhdankina, and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1094 (1993).

  60. E. R. Latypova, Candidate Dissertation, Inst. Org. Chem., Ufa Sci. Cent., RAS, Ufa, 2005, 112 pp.

  61. R. Ya. Kharisov, E. R. Latypova, R. F. Talipov, R. R. Muslukhov, G. Yu. Ishmuratov, and G. A. Tolstikov, Russ. Chem. Bull., Int. Ed., 52, 2267 (2003).

    Article  CAS  Google Scholar 

  62. G. Yu. Ishmuratov, E. R. Latypova, R. Ya. Kharisov, R. R. Gazetdinov, A. V. Bannova, V. S. Tukhvatshin, and R. F. Talipov, Vestn. Bash. Univ., 14, 19 (2009).

    Google Scholar 

  63. J. N. Marx and L. R. Norman, J. Org. Chem., 40, 1602 (1975).

    Article  CAS  Google Scholar 

  64. K. Mori, Molecules, 10, 1023 (2005).

    Article  CAS  Google Scholar 

  65. C. G. Overberger and J. K. Weise, J. Am. Chem. Soc., 90, 3525 (1968).

    Article  CAS  Google Scholar 

  66. C. J. Moore, A. Hubener, and Y. Q. Tu, J. Org. Chem., 59, 6136 (1994).

    Article  CAS  Google Scholar 

  67. Y. Q. Tu, C. J. Moore, and W. Kitching, Tetrahedron: Asymmetry, 6, 397 (1995).

    Article  CAS  Google Scholar 

  68. K. Mori and H. Watanabe, Tetrahedron, 40, 299 (1984).

    Article  CAS  Google Scholar 

  69. T. Sugai and H. Ohta, Agric. Biol. Chem., 53, 2009 (1989).

    Article  CAS  Google Scholar 

  70. R. Noyori, T. Ohkura, and M. Kitamura, J. Am. Chem. Soc., 109, 5856 (1987).

    Article  CAS  Google Scholar 

  71. H. Kiyota and K. Mori, Biosci. Biotechnol. Biochem., 58, 1120 (1994).

    Article  CAS  Google Scholar 

  72. S. Muto, M. Bando, and K. Mori, Eur. J. Org. Chem., 1946 (2004).

  73. D. Pempo, J. Viala, J. L. Parrican, and M. Santelli, Tetrahedron: Asymmetry, 7, 1951 (1996).

    Article  CAS  Google Scholar 

  74. L. Poppe, L. Novak, J. Devenyi, and C. Szantay, Tetrahedron Lett., 32, 2643 (1991).

    Article  CAS  Google Scholar 

  75. G. Gries, G. G. S. King, R. Gries, P. D. C. Wimalaratne, T. G. Gray, R. F. Shepherd, J. Li, K. N. Slessor, and G. Khaskin, J. Chem. Ecol., 19, 1501 (1993).

    Article  CAS  PubMed  Google Scholar 

  76. H. Takikawa, Y Shirai, M. Kobayashi, and K. Mori, Liebigs Ann. Chem., 1965 (1996).

  77. K. Mori and J. Wu, Liebigs Ann. Chem., 213 (1991).

  78. K. Mori, Tetrahedron, 39, 3107 (1983).

    Article  CAS  Google Scholar 

  79. D. J. Aberhard and C. T. Hsu, J. Chem. Soc. Perkin Trans. 1, 1404 (1979).

    Article  Google Scholar 

  80. H. Takikawa, H. Tamagawa, and K. Mori, J. Indian Chem. Soc., 74, 855 (1997).

    CAS  Google Scholar 

  81. Y. Shirai, M. Seki, and K. Mori, Eur. J. Org. Chem., 3139 (1999).

  82. V. N. Odinokov, V. R. Akhmetova, Kh. D. Khasanov, A. A. Abduvakhabov, V. R. Sultanmuratova, and G. A. Tolstikov, Zh. Org. Khim., 28, 1173 (1992).

    CAS  Google Scholar 

  83. E. M. Santangelo, A. G. Correa, and P. H. G. Zarbin, Tetrahedron Lett., 47, 5135 (2006).

    Article  CAS  Google Scholar 

  84. K. Mori and H. Horikiri, Liebigs Ann. Chem., 501 (1996).

  85. G. Yu. Ishmuratov, R. R. Gazetdinov, V. A. Vydrina, R. Ya. Kharisov, M. P. Yakovleva, E. G. Akhmetzyanova, G. R. Talipova, and R. F. Talipov, Vest. Bashk. Univ., 17, 1700 (2012).

    Google Scholar 

  86. G. Yu. Ishmuratov, O. V. Botsman, L. P. Botsman, M. P. Yakovleva, R. Ya. Kharisov, and G. A. Tolstikov, Chem. Nat. Compd., 36, 207 (2000).

    Article  CAS  Google Scholar 

  87. K. Kh. Nguen, M. V. Mavrov, and E. P. Serebryakov, Bioorg. Khim., 14, 250 (1988).

    Google Scholar 

  88. S. Narasimnah and H. Mohan, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 34, 950 (1995).

    Google Scholar 

  89. G. Yu. Ishmuratov, M. P. Yakovleva, R. Ya. Kharisov, O. V. Botsman, O. I. Izibairov, A. G. Mannapov, and G. A. Tolstikov, Chem. Nat. Compd., 37, 190 (2001).

    Article  CAS  Google Scholar 

  90. V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, and G. A. Tolstikov, Chem. Nat. Compd., 28, 235 (1992).

    Article  Google Scholar 

  91. G. Z. Huang, J. M. Li, J. L. Lu, and H. A. Aisa, Chem. Nat. Compd., 42, 727 (2006).

    Article  CAS  Google Scholar 

  92. V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, and G. A. Tolstikov, Chem. Nat. Compd., 22, 595 (1986).

    Article  Google Scholar 

  93. G. Yu. Ishmuratov, R. Ya. Kharisov, and M. P. Yakovleva, Insect Endo- and Exohormones: Characteristics, Synthesis and Use [in Russian], Gos. Izd. Nauchn.-Tekh. Lit. “Reaktiv,” Ufa, 2000, 34 pp.

  94. R. P. Kavirayani and A. Pazhamalai, Tetrahedron: Asymmetry, 18, 1419 (2007).

    Article  Google Scholar 

  95. Y. Schmidt, L. Konrad, and U. Breuninger, J. Org. Chem., 75, 4424 (2010).

    Article  CAS  PubMed  Google Scholar 

  96. Y. Schmidt and B. Breit, Org. Lett., 11, 4767 (2009).

    Article  CAS  PubMed  Google Scholar 

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Correspondence to G. Yu. Ishmuratov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2015, pp. 177–196.

G. A. Tolstikov (Deceased).

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Ishmuratov, G.Y., Legostaeva, Y.V., Garifullina, L.R. et al. Ozonolysis of Unsaturated Compounds in the Synthesis of Insect Pheromones and Juvenoids. Chem Nat Compd 51, 199–219 (2015). https://doi.org/10.1007/s10600-015-1246-3

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