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Ozonolysis of dipterocarpol and its derivatives

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Abstract

Oxidation of dipterocarpol and its derivatives with ozone gave compounds containing lactone, lactol, alkoxytetrahydrofuran, aldehyde, and methyl ketone fragments in the side chain, as well as 1,2,4-trioxolane fragment in the A ring. The molecular and crystalline structures of dipterocarpol were determined by X-ray analysis.

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References

  1. Akihisa, T., Tokuda, H., Ukiya, M., Suzuki, T., Enjo, F., Koike, K., Nikaido, T., and Nishino, H., Chem. Pharm. Bull., 2004, vol. 52, p. 153.

    Article  CAS  Google Scholar 

  2. Hirabayashi, K., Iwata, S., Matsumoto, H., Mori, T., Shibata, Sh., Baba, M., Ito, M., Shigeta, Sh., Nakashima, H., and Yamamoto, N., Chem. Pharm. Bull., 1991, vol. 39, p. 112.

    Article  CAS  Google Scholar 

  3. Inada, A., Somekawa, M., Murata, H., Nakanishi, T., Tokuda, H., Nishino, H., Iwashima, A., Darnaedi, D., and Murata, J., Chem. Pharm. Bull., 1993, vol. 41, p. 617.

    Article  CAS  Google Scholar 

  4. Poechland, B.I., Carte, B.K., and Francis, T.A., J. Nat. Prod., 1987, vol. 50, p. 706.

    Article  Google Scholar 

  5. Platonov, G.V., Zorina, A.D., Gordon, M.A., Chizhov, N.P., Balykina, L.V., Mikhailov, Yu.D., Ivanen, D.R., Tran Kim Kvi, and Shavva, A.G., Khim.-Farm. Zh., 1995, no. 2, p. 42.

  6. Akihisa, T., Ogihara, J., Kato, J., Yasukawa, K., Ukiya, M., Yamanouchi, S., and Oishi, K., Lipids, 2001, vol. 36, p. 507.

    Article  CAS  Google Scholar 

  7. Révész, L., Hiestand, P., La Vecchia, L., Naef, R., Naegeli, H.-U., Oberer, L., and Roth, H.-J., Bioorg. Med. Chem. Lett., 1999, vol. 9, p. 1521.

    Article  Google Scholar 

  8. Scholz, D., Baumann, K., Grassberger, M., Wolff-Winiski, B., Rihs, G., Walter, H., and Meingassner, J.G., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 2983.

    Article  CAS  Google Scholar 

  9. Zorina, A.D., Balykina, L.V., Nazarova, O.V., and Rebezov, A.A., Zh. Prikl. Khim., 2006, vol. 79, p. 663.

    Google Scholar 

  10. Crabbé, P., Ourisson, G., and Takahashi, T., Tetrahedron, 1958, vol. 3, p. 279.

    Article  Google Scholar 

  11. Mills, J.S., J. Chem. Soc., 1956, p. 2169.

  12. Shibata, S., J. Korean Med. Sci., 2001, vol. 16, p. 28.

    Google Scholar 

  13. Dinda, B., Debnath, S., Mohanta, B.C., and Harigaya, Y., Chem. Biodiv., 2010, vol. 7, p. 2327.

    Article  CAS  Google Scholar 

  14. Christensen, L.P., Food Nutr. Res., 2009, vol. 55, p. 1.

    Article  CAS  Google Scholar 

  15. Rogers, D., Acta Crystallogr., 1962, vol. 15, p. 514.

    Article  CAS  Google Scholar 

  16. Kukovinets, O.S., Kasradze, V.G., Galin, F.Z., Spirikhin, L.V., Zainullin, R.A., Kislitsin, M.I., Abdullin, M.I., Kunakova, R.V., and Tolstikov, G.A., Russ. J. Org. Chem., 2002, vol. 38, p. 511.

    Article  CAS  Google Scholar 

  17. Kazakova, O.B., Kazakov, D.V., Yamansarov, E.Yu., Medvedeva, N.I., Tolstikov, G.A., Suponitsky, K.Yu., and Arkhipov, D.E., Tetrahedron Lett., 2011, vol. 52, p. 976.

    Article  CAS  Google Scholar 

  18. APEX2 and SAINT, Madison, Wisconsin, USA: Bruker AXS, 2005.

  19. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    I. E. Smirnova, O. B. Kazakova, G. A. Tolstikov, O. S. Kukovinets & A. N. Lobov

  2. Institute of Chemistry, Vietnam Academy of Sciences and Technologies, Hanoi, Vietnam

    H. Do Thi Thu

  3. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    K. Yu. Suponitskii

Authors
  1. I. E. Smirnova
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  2. H. Do Thi Thu
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  3. O. B. Kazakova
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  4. G. A. Tolstikov
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  5. O. S. Kukovinets
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  6. A. N. Lobov
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  7. K. Yu. Suponitskii
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Corresponding author

Correspondence to O. B. Kazakova.

Additional information

Original Russian Text © I.E. Smirnova, Kh. Do Tkhi Tkhu, O.B. Kazakova, G.A. Tolstikov, O.S. Kukovinets, A.N. Lobov, K.Yu. Suponitskii, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1374–1379.

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Smirnova, I.E., Do Thi Thu, H., Kazakova, O.B. et al. Ozonolysis of dipterocarpol and its derivatives. Russ J Org Chem 48, 1370–1376 (2012). https://doi.org/10.1134/S1070428012100193

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  • DOI: https://doi.org/10.1134/S1070428012100193

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