Abstract
The13C NMR spectra of a number of α-homologs of 11-deoxyprostaglandin E1 have been investigated and a stereochemical assignment has been made of the diasteromeric pairs of isomers with lengths of the α-chain from seven to twelve carbon atoms. The most informative characteristics for the separation of the classes of epimers have been determined; these are differences in the chemical shifts of the C13 and C15 carbon atoms.
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Literature cited
W. Bortmann, J. Bock, et al., in: Chemistry, Biochemistry, and Pharmacological Activity of Prostaglandins (ed. by M. Roberts and F. Scheinmann), Pergamon, Oxford (1979), p. 193.
G. Lukacs, F. Pirion, D. S. Gero, et al., Tetrahedron Lett., 515 (1973).
G. F. Cooper and I. Fried, Proc. Mat. Acad. Sci., USA,70, 1579 (1973).
G. C. Levy, R. L. Lichter, and L. Nelson, Carbon-13 Nuclear Magnetic Resonance Spectroscopy, Wiley-Interscience, New York, 2nd ed. (1980), p. 264.
T. Pekhk, T. Vyalimyae, H. Samel', et al., Izv. Akad. Nauk SSSR, Khim., No. 2, 85 (1982).
L. M. Khalilov, R. A. Sadykov, A. A. Fatykhov, et al., in: Abstracts of Lectures at the VIth All-Union Conference [in Russian], Novosibirsk (1983), p. 54.
M. Christl, H. J. Reich, and J. D. Roberts, J. Am. Chem. Soc.,93, No. 14, 3463 (1971).
A. Tolstikov, M. S. Miftakhov, F. A. Valeev, et al., Zh. Org. Khim.,19, 279 (1983).
Additional information
Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 315–319, May–June, 1985.
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Tolstikov, G.A., Khalilov, L.M., Panasenko, A.A. et al. 13C NMR spectra of biologically active compounds. I. α-Homologs of 11-deoxyprostaglandin E1 . Chem Nat Compd 21, 293–297 (1985). https://doi.org/10.1007/BF00574196
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DOI: https://doi.org/10.1007/BF00574196