Abstract
Stereochemical features of the structure of the germacrane lactones have been investigated. By correlating the circular dichroism and the results of x-ray structural analyses of the germacranolides with different types of linkage of the lactone ring it has been estabished that Geissman's rule is satisfied in the trans-trans-germacral(10), 4-dienolide series if the lactone ring has the S-conformation and the decadiene ring the chair-chair conformation in the C6-trans-lactones and, correspondingly, the A and chair-chair conformations in the C6-cis compounds. The decadiene ring has the boat-boat conformation if there is an exocyclic double bond at C10 in the C8-trans-germacrolides, and a positive Cotton effect (CE) is observed in the CD spectra in the 220 nm region and a negative one at 200 nm.
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Literature cited
T. G. Waddell, W. Stöcklin, and T. A. Geissman, Tetrahedron Lett.,17, 1313 (1969).
A. F. Beecham, Tetrahedron,28, 5543 (1972).
A. T. McPhail, K. D. Onan, and P. M. Gross, J. Chem. Soc. Perkin Trans. II, 578 (1976).
A. T. PcPhail and G. A. Sim, Tetrahedron,29, 1751 (1973).
Z. Samek and J. Harmatha, Collect. Czech. Chem. Commun.,43, 2779 (1978).
Z. Samek, Collect. Czech. Chem. Commun.,43, 3210 (1978).
G. P. Moiseeva, I. M. Yusupova, B. Kh. Abduazimov, and G. P. Sidyakin, Khim. Prir. Soedin., 176 (1986).
M. K. Makhmudov, B. Kh. Abduazimov, B. Tashkhodzhaev, and B. T. Ibragimov, Khim. Prir. Soedin., 59 (1988).
M. K. Makhmudov, B. Kh. Abduazimov, B. Tashkhodzhaev, and B. T. Ibragimov, Khim. Prir. Soedin., 198 (1989).
R. W. Doskotch, E. H. Fairchild, C. T. Huang, J. H. Wilton, M. A. Beno, and G. G. Christoph, J. Org. Chem.,45, 1441 (1980).
M. Suchy, L. Dolejs, V. Herout, F. Sorm, G. Snatzke, and J. Himmelreich, Collect. Czech. Chem. Comm.,34, 229 (1969).
A. T. McPhail, K. D. Onan, and P. M. Gross, J. Chem. Soc. Perkin Trans. II, 1798 (1975).
W. Herz and R. De Groote, Phytochemistry,16, 1307 (1977).
W. Herz and N. Kumar, J. Org. Chem.,45, 489 (1980).
A. Quick and D. Roger, J. Chem. Soc. Perkin Trans. II, 465 (1976).
W. Herz, S. V. Govindan, and J. F. Blount, J. Org. Chem.,45, 1113 (1980).
Z. Samek, M. Holub, U. Rychlewska, H. Grabarczyk, and B. Drozdz, Tetrahedron Lett., 2691 (1979).
H. Tada and K. Takeda, J. Chem. Soc., Chem. Commun., 1979 (1971).
K. Tori, J. Horibe, K. Kuriyama, H. Tada, and K. Takeda, Chem. Commun., 1393 (1971).
H. D. Fisher, N. H. Fisher, R. W. Franek, and E. J. Oliver, Progr. Chem. Org. Nat. Prod.,37, 94 (1979).
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Institute of Chemistry of Plant Substances Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 742–748, November–December, 1990.
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Moiseeva, G.P., Abduazimov, B.K. Stereochemical features of the structure of germacrane lactones and the applicability of Geissman's rule in this series. Chem Nat Compd 26, 630–635 (1990). https://doi.org/10.1007/BF00630070
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DOI: https://doi.org/10.1007/BF00630070