Conclusions
The stereoisomerism in series of androstano- and estrano-D′-pentaranes in solution has been investigated by13C NMR. The orientation of the D′ ring in the 15α,16α-, 15β,16β-, and 15α,16β-isomers relative to the steroid skeleton, as well as the “boat” conformation of the D′ ring, were determined from the13C chemical shifts.
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A. V. Kamernitskii, T. N. Galakhova, I. S. Levina, V. A. Pavlov, and B, S. Él'yanov, Izv. Akad. Nauk SSSR, Ser. Khim., 2147 (1982).
A. A. Akhrem, L. E. Kulikova, I. S. Levina, and Yu. A. Timov, Izv. Akad. Nauk SSSR, Ser. Khim., 1358 (1972).
J. W. Blunt and J. B. Stothers, Org. Magn. Reson.,9, 439 (1977).
C. L. Van Antwerp, H. Eggert, G. D. Meakins, J. O. Miners, and C. Djerassi, J. Org. Chem.,42, 789 (1977).
H. Beierbeck and J. K. Saunders, Can. J. Chem.,54, 2985 (1976).
K. N. Scott and T. H. Marect, Can. J. Chem.,57, 27 (1979).
J. B. Lambert and A. K. Vagenas, Org. Magn. Reson.,17, 265 (1981).
H. Eggert, C. L. Van Antwerp, N. S. Bhacca, and C. Djerassi, J. Org. Chem.,41, 71 (1976).
J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York-London (1972), p. 165.
S. H. Grover and J. B. Stothers, Can. J. Chem.,52, 870 (1974).
J. W. Apsimon, H. Beierbeck, and T. K. Saunders, Can. J. Chem.,53, 338 (1975).
G. C. Levy and U. Edlund, J. Am. Chem. Soc.,97, 5031 (1975).
D. Leibfritz and J. D. Roberts, J. Am. Chem. Soc.,95, 4998 (1973).
T. C. Farrar and E. D. Becker, Pulse and Fourier Transform NMR, Academic Press, New York (1971).
H. Hart and G. M. Love, Tetrahedron Lett., 625 (1971).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1038–1045, May, 1984.
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Bogdanov, V.S., Cherepanova, E.G., Galakhova, T.N. et al. 13C NMR spectra and stereoisomerism in series of androstano-and estrano-D′-pentaranes. Russ Chem Bull 33, 955–961 (1984). https://doi.org/10.1007/BF01141704
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DOI: https://doi.org/10.1007/BF01141704