Conclusions
-
1.
The Δ16(17)-20-keto group in 21-substituted pregnetiones is conformationally labile.
-
2.
From a comparison of the IR, UV, and CD spectra, the influence of substitution at C-21 on the configuration of theα, β-unsaturated ketochromophore was established.
Similar content being viewed by others
Literature cited
A. A. Akhrem, G. A. Kogan, A. V. Kamernitskii, I. G. Reshetova, T. N. Deshko, and I. S. Kovnatskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 550 (1973).
G. Snatzke (editor), Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry [Russian translation], Mir (1970), Chap. 4, p. 202.
G. Snatzke, Tetrahedron,21, 413 (1965).
A. W. Burgstahler and R. C. Barkhurst, J. Amer. Chem. Soc.,92, 7601 (1970).
F. H. Cottee, B. P. Straughan, C. I. Timmons, W. F. Forbes, and Shilton, J. Chem. Soc., B, 1146 (1967).
I. K. Groves and N. Jones, Tetrahedron,25, 223 (1969).
S. Rakhit and Ch. R. Engel, Canad. J. Chem., 2163 (1962).
A. A. Akhrem, A. V. Kamernitskti, I. G. Reshetova, and K. Yu. Chernyuk, Izv. Akad. Nauk SSSR, Ser. Khim., 709 (1973).
W. P. Hayes and C. I. Timmons, Spectrochim. Acta,A24, 323 (1968).
L. Vellus and M. Legrand, Angew. Chemie,73, 603 (1961).
H. Ziffer and C. H. Robinson, Tetrahedron,24, 5803 (1968).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1995–1999, September, 1973.
Rights and permissions
About this article
Cite this article
Deshko, T.N., Kogan, G.A., Kamernitskii, A.V. et al. Optical rotatory dispersion and circular dicheoism in structueal and sterecchemical problems Communication 6. Study of the stereochemistry of the side chain of 21-substituted δ16(17)-20-ketopregnenes. Russ Chem Bull 22, 1945–1948 (1973). https://doi.org/10.1007/BF00929381
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00929381