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Abstrakty
Convergent synthesis of ent-1alfa,25-dihydroxyvitamin D3 (ent-calcitriol, 2) and (1S,3S, 13S,14S,17S,20S) - 1alfa,25-dihydroxyvitamin D3 (5) using the ring A building blocks, 6 and 7, respectively, and rings CD building block8, is described. Building block 6 was obtained starting from vitamin D3 via dihydroxylation of the C7-C8 double bond, Mitsunobu inversion at C3, diastereoselective hydroxylation at C1 and cleavage of the C7-C8 bond. Building block 7 was prepared from known synthetic intermediate, 16a(1R,3S) via benzylation of the primary hydroxy group, mono-deprotection of bis-silyl ether 16b and Mitsunobu inversion of the configuration at C3 in 19. Synthetic building blocks were combined using Julia-Kocienski olefination reaction. Key words:Vitamins D, convergent synthesis, Mitsunobu reaction, olefination reaction
Słowa kluczowe
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Czasopismo
Rocznik
Tom
Strony
413--428
Opis fizyczny
Bibliogr. poz. 40
Twórcy
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warszawa 42, Poland
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warszawa 42, Poland
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warszawa 42, Poland
Bibliografia
- 1. Bouillon R., Okamura W.H. and Norman A.W., Endoc. Rev., 16, 200 (1995).
- 2. Beckman M.J. and DeLuca H.F., in Progr: Med Chem., WI. 35 (Eds; G.P. Ellis, D.K. Luseombe, A.W. Oxford), Elsevier, Amsterdam, pp. 1, (1998).
- 3. Posner G.H. and Kaluarnan M., Eur. .J. Org. Chem, 3889 (2003).
- 4. Kabat M.M. and Radinov R., Curr: Opin. Drug Discovery Dev., 4, 808 (2001).
- 5.Nonnan A.W., Nemere I., Zhou L.X., Bishop J.E., Lowe K.E., Maiyer A.C., Collins E.D., Taoka T., Sergeev I. and Farach-Carson M.C., .J Steroid Biochem. Molec. Biol., 41, 231 (1992).
- 6. Binderup L., Latini S., Binderup E., Bertting C., Calverley M. and Hansen K., Biochem. Pharmacol. , 42, 1569 ( 1991).
- 7. DeLuca H.F. and Wicha J., US. Patent 5,552,392 (1996; Appl. Non 3, 1993).
- 8. Kurek-Tyrlik A., Makaev F.Z., Wicha J . and Calverley M.J., Liebigs Ann./Recueil, 1997 (1997).
- 9. Maehr H. and Uskokovic M.R., Eur: J. Org. Chem., 1703 (2004).
- 10. Yong W., Ling S., Dhalleweyn C., Van Haver D., DeClercq P. and Vandewalle M., Bioorg. Med Chem. Lett, 7, 923 (1997).
- 11. Kutner A., Zhao H., Fitak H. and Wilson S.R., Bioorganic Chem., 23, 22 (1995).
- 12. Gabriels S., Van Haver D., Vandewalle M., Clercq P. De, Verstuyf A. and Bouillon R., Chem. -Eur: . 7, 520 (2001).
- 13. Biellmann J.F., Chem. Rev., 103, 2019 (2003).
- 14. Ariens E.J., Trends Pharmacol. Sci, 7, 200 (1986).
- 15. Buzby G.C., Hartley D., Hughes G.A. and Smith H., J Med. Chem., 10, 199 (1967).
- 16. Boyd A., Groen M.B., Hindriksen B., Marshall R..I., Sleigh T., lhrmslow E. and Zeelen F.J., Steroids, 4 615 (1982).
- 17.Westover E.J., Covey D.F., Brockman H.L., Brown R.E. and Pike L.J., J. Biol. Chem., 278, 5111 (2003).
- 18.Achmatowicz B., Gorobets E., Marczak S., Przezdziecka A., Steinmeyer A., Wicha J. and Zugel U., Tetrahedron Lett., 42, 2891 (2001).
- 19. Gorobets B., Stepanenko V. and Wicha J., Eur. J. Org Chem., 783 (2004).
- 20.Zhu G.-D. and Okamura W.H., Chem. Rev., 95, 1877 (1995).
- 21. Dai H. and Posner G.H., Synthesis, 1383 (1994).
- 22. Hanazawa T., Koyama A., Wada T., Morishige E., Okamoto S. and Sato F., Org. Lett., 5, 3 167 (2003).
- 23. Hiyarnizu H1., Ooi H., Inomoto Y., Bsumi T., Iwabuchi Y. and Hatakeyama S., Org. Lett. , 3, 473 (2001).
- 24. Konno K., Maki S., Fujishima T., Liu Z.P., Miura D., Chokki M. and Takayama H., Bioorg. Med. Chem. Lett., 8, 2817 (1998).
- 25. Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T. and Takayama H., Bioorg. Med. Chem., 123 (2000).
- 26. Achmatowicz B., Jankowski P. and Wicha J., Tetrahedron Lett., 37, 5589 (1996).
- 27. Paaren H.E., DeLuca H.F. and Schnoes H.K., J. Org. Chem., 45, 3253 (1980).
- 28. Toh H.T. and Okamura W.H., J Org. Chem., 48, 1414 (1983).
- 29. Wang Y., Ting H.-S., Huang I.-J., Chow Y.-C. and Huang Y.-T., Acta Chim. Sin., 24, 126 (1958).
- 30.Mitsunobu O., .Synthesis, 1 (1981).
- 31. Sammakia T. and Jacobs J.S., Tetrahedron Lett., 40, 2685 (1999).
- 32. Tahara Y., in U. S. Patent 5,283,345 (1994, Application May 6, 1992).
- 33. Blakemore P.R., Kocienski P.J., Marcmk S. and Wicha J ., Synthesis, 1209 (1999).
- 34. Luche J.-L., Rodriguez-Hahn L. and Crabbe P., J. Chem. Soc. Chem. Commun., 601 (1978).
- 35. Diaz M., Ferrero M., Fernandez S. and Gotor V., Tetrahedron Lett., 41, 775 (2000).
- 36.Dess D.B. and Martin J.C., J. Org. Chem., 48, 4155 (1983).
- 37. Julia M. and Paris I.-M., Tetrahedron Lett., 4833 (1973).
- 38. Kocienski P.J., Lythgoe B. and Ruston S., J. Chem. Soc., Perkin Trans. 1, 1290 (1979).
- 39. Blakemore P.R., Grzywacz P., Kocienski P. ., Marczak S. and Wicha J.,PoIish.J Chem. , 73, 1209 (1999)
- 40. Baggiolini E.G., Iacobelli J.A., Hennessy B.M., Batcho A.D., Sereno J .F. and Uskokovic M. J Org. Chem., 51, 3098 (1986).
Typ dokumentu
Bibliografia
Identyfikator YADDA
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