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Abstrakty
Full assignment of 13C NMR shifts for a series of _8-5_- and 5_-steroids is presented. These data along with some characteristic features of 1H NMR and IR spectra are in accordance with inverted conformation of Aand B rings in 4-oxo-5_-steroids 5 and 6 in solution. Configuration at C-3 is important for inversion of Aand B ring conformation of _-methyl ketones 6 and 7, while the intramolecular hydrogen bonding appears to be responsible for the inverted, slightly distorted chair conformation of ring A in _-hydroxy ketone 5.
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
1599--1606
Opis fizyczny
Bibliogr. 28 poz., rys.
Twórcy
autor
- Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
autor
- Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
autor
- Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
Bibliografia
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- 4. Bhagavan N.V., Medical Biochemistry, Academic Press, 2002, Ch. 26 and 30.
- 5. Kollman P.A., Giannini D.D., Duax W.L., Rothenberg S. and WolfFM. E., J. Am. Chem. Soc., 9i (1973).
- 6. Desai U.R. and Trivedi G.K., Indian J. Chem., 30 B, 915 (1991) and references cited therein.
- 7. Angell E.C., Fringuelli F., Pizzo F., Porter B., Taticchi A. and Wenkert E., J. Org. Chem., 51, 2642 (1986).
- 8. Angell E.C., Fringuelli F., Pizzo F., Minuti L., Taticchi A. and Wenkert E., J. Org. Chem., 54, 1217 (1989).
- 9. Angell E.C., Fringuelli F., Minuti L., Pizzo F., Porter B., Taticchi A. and Wenkert E., J. Org. Chiem., 51, 2649 (1986).
- 10. Eliel E.L. and Wilen S. H., Stereochemistry of Organic Compounds, Wiley, 1994, Ch. 11.
- 11. Wallimann P., Marti T., Furer A. and Diederich F., Chem. Rev., 97, 1567 (1997); Tamminet Kolehmainen E., Molecules, 6, 21 (2001).
- 12. Barton D.H.R. and Morrison G.A., Fortschr. Chem. Org. Nalurst., 19, 165 (1961).
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- 16. Paryzek Z. and Martynow J., J. Chem. Soc. Perkin Trans. I, 599 (1990).
- 17. Paryzek Z. and Martynow J., J. Chem. Soc. Perkin Trans. 1, 243(1991).
- 18. Lukács G., Khuong Huu F., Bennett C.R., Buckwalter B.L. and Wenkert E., Tetrahedron Lett. 3515, (1972).
- 19. Ben Harref A. and Lavergne J.-P., Bull. Soc. Chim. Fr., 965 (1985).
- 20. Martynow J. and Paryzek Z., Magn. Reson. Chem., 27, 258 (1989) and references cited therein.
- 21. Blunt J.W. and Stothers J.B., Org. Magn. Reson.. 9,439 (1977); Duddeck H., Top. Stereochem. (1986).
- 22. Gough J.L., Guthrie J.P. and Stothers J.B., J. Chem. Soc., Chem. Commun., 979 (1972).
- 23. Engelhardt G., Zeigan D. and Schönecker B., J. Prakt. Chem., 320, 377 (1978).
- 24. Zürcher R.F., Helv. Chim. Acta, 46, 2054 (1963).
- 25. Bull J.R. and Tuinmann A., J. Chem. Soc. Perkin Trans. 1, 212 (1976).
- 26. Kirk D.N. and McHugh C.R., J. Chem. Soc. Perkin Trans. 1, 173 (1978).
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- 28. Defaye G. and Fetizon M., Bull. Chem. Soc. Fr., 1632 (1969).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0022-0024