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Abstrakty
The reaction of cholesteryl acetate with ozone in the presence of amines has been studied. Besides the expected cleavage products, B-seco-ketoaldehyde and its aldol condensation product, 5-hydroxy-6-formyl-B-nor-5_-cholestane derivative, the abnormal product, 3_-acetoxy-A-nor-3(5_6_)abeo-6_(H)-cholestan-5-one is formed as a result of a new, anomalous cleavage of the primary ozonide. The reaction conditions and isolation procedure were optimized for achieving good yield of the abeo-compound. The X-ray crystal structure analysis confirmed the formation of the unusual steroidal skeleton. It appears to be the first crystallographic analysis of the transformed steroid with A-nor-3(5_6_)abeo skeleton. No product resulting from the amine nucleophilic participation in the cleavage of ozonides was observed.
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
921--930
Opis fizyczny
Bibliogr. 28 poz., rys.
Twórcy
autor
- Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
autor
- Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
autor
- Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
autor
- Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
Bibliografia
- 1. Bailey P.S., in Ozonation in Organic Chemistry, Academic Press, NY, vol. 2, Ch. 7 (1982).
- 2. Bailey P.S., in Ozonation in Organic Chemistry, Academic Press, NY, vol. 1, a) Ch. 7, b) Ch. 9 (1978),
- 3. Fremery M.I. and Fields E.K., J. Org. Chem., 29, 2240 (1964).
- 4. Hon Y.S., Lin S.W., Lu L. and Chen Y.J., Tetrahedron, 51, 5019 (1995).
- 5. Schulz M., Becker D. and Rieche A., Angew. Chem, Int. Ed., 548 (1965).
- 6. Aurell M.J., Ceita L., Mestres R. and Tortajada A., Tetrahedron, 53, 10883 (1997).
- 7. Gumulka J. and Smith L.L., J. Am. Chem. Soc., 105, 1972(1983); Smith L.L., Ezell E.L. and Jaworski K„ Steroids, 61, 401 (1996).
- 8. Smith L.L., Lipids, 31, 453 (1996) and references cited therein.
- 9. a) ParyzekZ., MartynowJ. and Swoboda W., J. Chem. Soc., Perkin Trans. 1,1222 (1990); b) Paiyzek Z. and Rychlewska U., J. Chem. Soc., Perkin Trans. 2,2313 (1997) and references cited therein.
- 10. Ushigoe Y., Satake S., Masuyama A.,Nojima M. and McCullough K.J., J. Chem. Soc., Perkin Trans. 1, 1939(1997).
- 11. Jaworski K. and Smith L.L., J. Org. Chem., 53, 555 (1988).
- 12. Tanabe K., Hayashi R. and Takasaki R., Chem. Pharm. Bull., 9, 1 (1961).
- 13. Yates P. and Stiver S., Can. J. Chem., 66, 1209 (1988).
- 14. Morand P. and Kaufman M., J. Org. Chem., 34, 2175 (1969).
- 15. Dave V. and Stothers J.B., Can. J. Chem., 57,1550 (1979).
- 16. Morisawa Y., Chem. Pharm. Bull., 12, 1066 (1964).
- 17. a) Martin J., Parker W., Shroot B. and Steward T., J. Chem. Soc. C, 101 (1967); b) Kasai A., Collect. Czech. Chem. Commun., 43,1778 (1978).
- 18. Snatzke G. and Kinsky K., Tetrahedron, 28, 289 (1972).
- 19. Marchon J-C. and Ramasseul R., Synthesis, 389 (1989).
- 20. Hanson J.R. and Terry N., J. Chem. Res. (S), 50 (1998).
- 21. Nagata W., Narisada M., Wakabayashi T., Hayase Y. and Masayuki M., Chem. Pharm. Bull., 19, 1567 (1971).
- 22. Alien RH. and Kennard O., Chemical Design Automation News, 8, 1&31-37 (1993).
- 23. Turner R.B., J Am. Chem. Soc., 72, 579 (1950).
- 24. Weill-Raynal J., Synthesis, 49 (1969) and references cited therein; Julia S.A., Eschenmoser A., Heuser H. and Tarkey N„ Helv. Chim. Acta, 36, 1885 (1953).
- 25. Kehrli A.R.H., Taylor D.A.H. and Niven M., J. Chem. Soc., Perkin Trans. I, 2057 (1990).
- 26. Sheidrick G.M., Acta Cryst., A46, 467 (1990).
- 27. Sheidrick G.M., SHELXL-97, University of Gottingen, (1997).
- 28. Stereochemical Workstation Operation Manual, Release 3.4, Siemens Analytical X-Ray Instruments, Inc., Medison, Wisconsin, USA, (1989).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0023-0004