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.
Similar content being viewed by others
Literature cited
M. Miski, T. Mabry, and O. Saya, Phytochemistry,26, No. 6, 1733 (1987).
M. Holub and Z. Samek, Collect. Czech. Chem. Commun.,42, 1053 (1977).
H. Itokawa, H. Matsumoto, S. Mihashi, and Y. Iitaka, Chem. Lett., 1581 (1988).
M. K. Makhmudov, B. Tashkhodzhaev, G. B. Sagitdinova, A. I. Saidkhodzhaev, M. R. Yagudaev, and V. M. Malikov, Khim. Prir. Soedin., 42 (1986).
O. Yu. Rekhlova, B. Tashkhodzhaev, V. I. Andrianov, A. I. Saidkhodzhaev, G. B. Sagitdinova, and N. G. Furmanova, Khim. Prir. Soedin., 757 (1990).
O. Yu. Rekhlova, B. Tashkhodzhaev, V. I. Andrianov, G. B. Sagitdinova, and A. I. Saidkhodzhaev, Khim. Prir. Soedin., 494 (1991).
Y. Naya, K. Yoshihara, T. Iwashita, H. Komura, K. Nakanishi, and Y. Hata, J. Am. Chem. Soc.,103, 7009 (1981).
N. H. Fischer, E. J. Oliver, and H. D. Fischer, Prog. Chem. Org. Nat. Prod.,38, 48 (1979).
A. S. Gupta and S. Dev, Tetrahedron,27, 635 (1971).
U. Burkert and N. L. Allinger, Molecular Mechanics, ACS Monograph 177, American Chemical Society, Washington, D.C. (1982).
V. G. Dashevskii, The Conformation of Organic Molecules [in Russian], Khimiya, Moscow (1974), p. 35.
N. L. Allinger, J. Am. Chem. Soc.,99, 8127 (1977).
Additional information
Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 197–202, March–April, 1992.
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00630167