Warianty tytułu
Konferencja
21st Conference on Isoprenoids, 23-29 September 2005, Białystok-Białowieża, Poland
Języki publikacji
Abstrakty
There is an increasing interest in developing new strategies to introduce functional groups into specific positions of steroidal nuclei in order to modify their biological properties. Transition metal catalyzed reactions have proved to be versatile tools both for the construction of the steroid framework from easily available building blocks and for the functionalization of the steroidal skeleton. By palladium-catalyzed carbonylation, carbon monoxide can be introduced directly into a number of different sites in an organic molecule leading to the synthesis of aldehydes, ketones, carboxylic acids and their derivatives, lactones, lactames, etc. The products can often be obtained in good yield and with high selectivity usually under very mild conditions. In addition, palladium-catalyzed carbonylation is compatible with many functional groups, and therefore, more advantageous than conventional methods. In the present paper the most important achievements in carbonylation of steroidal substrates is reviewed together with a more detailed discussion of our own results obtained in this field.
Słowa kluczowe
Czasopismo
Rocznik
Tom
Strony
587-604
Opis fizyczny
Bibliogr. 66 poz.
Twórcy
autor
autor
- Department of Organic Chemistry and Research Group for Petrochemistry of the Hungarian Academy of Sciences, University of Veszprém, H-8201 Veszprém, P.O. Box 158, Hungary
Bibliografia
- 1. Skoda-Fóldes R. and Kollar L., Chem. Rev., 103, 4095 (2003).
- 2. Stoner E., J. Steroid Biochem. Mol. BioL, 37, 375 (1990).
- 3. Holt D.A., Levy M.A., Oh H.J., Erb J.M., Heaslip J.I., Brandt M., Hsun-Lin L.H. and Metcalf B.W., J. Med. Chem., 33, 943 (1990).
- 4. Moser W.R., Wang A.W. and Kildahl N.K., J. Am. Chem. Soc., 110, 2816 (1988).
- 5. Crisp G.T., Chem. Soc. Rev., 27, 427 (1998).
- 6. Amatore C. and Jutand A., J. Organomet. Chem., 576, 254 (1999).
- 7. Amatore C. and Jutand A., Acc. Chem. Res., 33, 314 (2000).
- 8. Hills I.D. and Fu G.C., J. Am. Chem. Soc., 126, 13178 (2004).
- 9. Collman J.P., Hegedus L.S., Norton J. R. and Finkę R.G., Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mili Valley, CA, 1987, p. 355.
- 10. Paquette L.A., Encyclopedia of Reagents for Organie Synthesis, John Wiley & Sons, New York, 1994, Vol. 7, p. 4788.
- 11. Amatore C., Jutand A. and M'Barki M.A., Organometallics, 11, 3009 (1992).
- 12. Amatore C., Carre E., Jutand A., M'Barki M.A. and Meyer G., Organometallics, 14, 5605 (1995).
- 13. NakamuraH., Shim J-G. and Yamamoto Y., J. Am. Chem. Soc., 119, 8113 (1997) and references cited therein.
- 14. Stang P.J., Hanack M. and Subramanian L.R., Synthesis, 85 (1982).
- 15. Crisp G.T. and Scott W.J., Synthesis, 335 (1985).
- 16. McGuire M.A., Sorenson E., Owings F.W., Resnick T.M., Fox M. and Baine N.H., J. Org. Chem., 59, 6683(1994).
- 17. Zhu Z., Tian W. and Liao Q., Tetrahedron Lett., 37, 8553 (1996).
- 18. Cox P.J. and Turner A.B., Tetrahedron, 40, 3153 (1984).
- 19. Barton D.H.R., Bashiardes B. and Fourrey J.L., Tetrahedron, 44, 147 (1988).
- 20. Schweder B. and Uhlig E., J. Prakt. Chem., 333, 223 (1991).
- 21. Baine N.H., Kline D.N., Mewshaw R.E. and Owings F.F., Eur. Pat. 0643723,1995 (Smithkline Beecham Co.); C.A. 119, 271485k (1995).
- 22. Skoda-Fóldes R., Csakai Z., Kollar L., Horvath J. and Tuba Z., Steroids 60, 812 (1995).
- 23. Skoda-Fóldes R., Kollar L., Marinelli F. and Arcadi A., Steroids, 59, 691 (1994).
- 24. Petz A., Horvath J., Tuba Z., Pinter Z. and Kollar L., Steroids, 67, 777 (2000).
- 14. Skoda-Fóldes R., Szekvólgyi Z., Kollar L., Berente Z., Horvath J. and Tuba Z., Tetrahedron, 56, 3415 (2000).
- 15. Ciattini P.G., Morera E. and Ortar G., Tetrahedron Lett., 32, 6449 (1991).
- 16. Sonogashira K., Cross-coupling Reactions to sp Carbons in Metal-catalyzed Cross-coupling Reactions, Eds. F. Diederich and P.J. Stang, Wiley-VCH, Weinheim 1998, p. 213.
- 17. Arcadi A., Cacchi S., Carnicelli V. and Marinelli F., Tetrahedron, 50, 437 (1994).
- 18. Arcadi A., Cacchi S., Del Rosario M., Fabrizi G. and Marinelli F., J. Org. Chem., 61, 9280 (1996).
- 19. Arcadi A., Cacchi S., Fabrizi G. and Moro L., Eur. J. Org. Chem., 1137 (1999).
- 20. Yu M.S. and Baine N.H., Tetrahedron Lett., 40, 3123 (1999).
- 21. McGuire M.A., Sorenson E., Klein D.N. and Baine N.H., Synth. Commun., 28, 1611 (1998).
- 22. Sabbir A. and Sophie D., Bioorg. Med. Chem. Lett., 8, 409 (1998).
- 23. Cacchi S., Morera E. and Ortar G., Tetrahedron Lett., 26, 1109 (1985).
- 24. Anacardio R., Arcadi A., D'Annibale G. and Marinelli F., Synthesis, 831 (1995).
- 25. Cacchi S., Ciattini P.G., Morera E. and Ortar G., Tetrahedron Lett., 27, 3931 (1986).
- 26. Dolle R.E., Schmidt S.J. and Kruse L.I., Chem. Commun., 904 (1987).
- 27. Holt D. A., Levy M.A. and Metcalf B.W., Eur. Pat. O 343 954 A2, 1989 (Smithkline Beecham Co.); C. A. 112, 198890n (1990).
- 28. Holt D.A., Levy M.A., Ladd D.L., Oh H., Erb J.M., Heaslip J.I., Brandt M. and Metcalf B.W., J. Med. Chem.,33,937(1990).
- 29. Holt D.A., Metcalf B.W. and Levy M.A., Eur. Pat.427434, 1991 (Smithkline Beecham Co.); C.A. 115, 208323h(1991).
- 41. Rasmuson G.H., Tolman R.L. and Patel G.F., Eur. Pat. 0465141, 1992 (Merck&Co. Inc.); C.A. 116, 1521516b(1992).
- 42. Tian W., Zhu Z., Liao Q. and Wu Y, Bioorg. Med. Chem. Lett., 8, 1949 (1998).
- 43. McGuire M.A., Sorenson E., Owings F.W., Resnick T.M., Fox M. and Baine N.H., J. Org. Chem., 59, 6683 (1994).
- 44. Skoda-Fóldes R., Horvath J., Tuba Z. and Kollar L., J. Organomet. Chem., 586, 94 (1999).
- 45. Cacchi S. and Lupi A., Tetrahedron Lett., 33, 3939 (1992).
- 46. Skoda-Fóldes R., Csakai Z., Kollar L., Szalontai G., Horvath J. and Tuba Z., Steroids, 60,786 (1995).
- 47. Holt D.A., Levy M.A. and Metcalf B.W., US Pat 4,882,319,1989 (Smithkline Beecham Co.); C.A. 112, 179604f(1990).
- 48. Holt D.A., Levy M.A. and Metcalf B.W., Eur. Pat.O 375 347 Al, 1990 (Smithkline Beecham Co.); C.A. 114, 43309x (1991).
- 49. Morera E. and Ortar G., Tetrahedron Lett., 39, 2835 (1998).
- 50. Petz A., Galik G., Horváth J., Tuba Z., Berente Z., Pinter Z. and Kollar, L. Synth. Commun., 31, 335 (2001).
- 51. SzarkaZ., Skoda-Foldes R., Kollar L., Berente Z., Horvath J. and Tuba Z., Tetrahedron, 56,5253 (2000).
- 52. Kollar L., Szarka Z., Horyath J. and Tuba Z., Tetrahedron Len., 38, 4467 (1997).
- 53. Skoda-Foldes R., Szarka Z., Kollar L., Dinya Z., Horvath J. and Tuba Z., J. Org. Chem., 64,2134 (1999).
- 54. Szarka Z., Skoda-Foldes R., Horyath J., Tuba Z. and Kollar L., Steroids, 67, 581 (2002).
- 55. Cacchi S., Fabrizi G. and Marinelli F., Synlett, 997 (1996).
- 56. Joó F., Biphasic Catalysis-Homogeneous, in Encyclopediaof Catalysis, Ed. I.T. Horyath, Wiley & Sons New York 2002, Vol. l, p. 737.
- 57. Panster P. and Wieland S., Applied Homogeneous Catalysis with Organometallic Compounds, Eds. B. Cornils and W.A. Herrmann, Wiley-VCH Weinheim, 1996, p. 605.
- 58. Aqueous-Phase Organometallic Catalysis. Concepts and Applications, Eds. B. Cornils and W.A. Herrmann, Wiley-YCH, Weinheim 1998.
- 59. Jessop P.G., Ikariya T. and Noyori R., Chem. Rev., 99, 475 (1999).
- 60. Welton T., Chem. Rev., 99, 2071 (1999).
- 61. Gordon C.M., Appl. Cat. A: General, 222, 101 (2001).
- 62. Olivier-Bourbigou H. and Magna L., J. Mol. Cat. A, 182-183, 419 (2002).
- 63. Zhao D., Wu M., Kou Y. and Min E., Catal Today, 74, 157 (2002).
- 64. Keim W., Green Chem., 5, 105 (2003).
- 65. Skoda-Foldes R., Takacs E., Horvath J., Tuba Z. and Kollar L., Green Chem., 5, 643 (2003).
- 66. Müller E., Peczely G., Skoda-Foldes R., Takacs E., Kokotos G., Bellis E. and Kollar L., Tetrahedron, 61, 797 (2005).
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0006-0056