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Humulenoids from plants of the family Apiaceae spatial structure of α-apienes

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Abstract

A conformational analysis has been made by the method of molecular mechanics of the α-apienes — natural sesquiterpenes isolated from plants of the Apiaceae family. The results of the mathematical method with the inclusion of those x-ray structural studies have shown that in the molecules under consideration it is possible to expect the predominant realization of four conformations of the 11-membered ring:14A 78 ,14A 87 ,14A 87 , and14A 78 . These four conformations of unsubstituted α-apiene and its natural derivatives have been characterized energetically, and the barriers to their interconversions have been evaluated.

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Literature cited

  1. M. Miski, T. Mabry, and O. Saya, Phytochemistry,26, No. 6, 1733 (1987).

    Google Scholar 

  2. M. Holub and Z. Samek, Collect. Czech. Chem. Commun.,42, 1053 (1977).

    Google Scholar 

  3. H. Itokawa, H. Matsumoto, S. Mihashi, and Y. Iitaka, Chem. Lett., 1581 (1988).

  4. M. K. Makhmudov, B. Tashkhodzhaev, G. B. Sagitdinova, A. I. Saidkhodzhaev, M. R. Yagudaev, and V. M. Malikov, Khim. Prir. Soedin., 42 (1986).

  5. O. Yu. Rekhlova, B. Tashkhodzhaev, V. I. Andrianov, A. I. Saidkhodzhaev, G. B. Sagitdinova, and N. G. Furmanova, Khim. Prir. Soedin., 757 (1990).

  6. O. Yu. Rekhlova, B. Tashkhodzhaev, V. I. Andrianov, G. B. Sagitdinova, and A. I. Saidkhodzhaev, Khim. Prir. Soedin., 494 (1991).

  7. Y. Naya, K. Yoshihara, T. Iwashita, H. Komura, K. Nakanishi, and Y. Hata, J. Am. Chem. Soc.,103, 7009 (1981).

    Google Scholar 

  8. N. H. Fischer, E. J. Oliver, and H. D. Fischer, Prog. Chem. Org. Nat. Prod.,38, 48 (1979).

    Google Scholar 

  9. A. S. Gupta and S. Dev, Tetrahedron,27, 635 (1971).

    Google Scholar 

  10. U. Burkert and N. L. Allinger, Molecular Mechanics, ACS Monograph 177, American Chemical Society, Washington, D.C. (1982).

    Google Scholar 

  11. V. G. Dashevskii, The Conformation of Organic Molecules [in Russian], Khimiya, Moscow (1974), p. 35.

    Google Scholar 

  12. N. L. Allinger, J. Am. Chem. Soc.,99, 8127 (1977).

    Google Scholar 

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Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 197–202, March–April, 1992.

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Tashkhodzhaev, B., Saidkhodzhaev, A.I. Humulenoids from plants of the family Apiaceae spatial structure of α-apienes. Chem Nat Compd 28, 168–173 (1992). https://doi.org/10.1007/BF00630167

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  • DOI: https://doi.org/10.1007/BF00630167

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