Highly β-selective epoxidation of the Δ5- and Δ4-unsaturated steroids catalyzed by the silica-supported polyhalogenated ruthenium porphyrin

Applied Catalysis A: General

Volumn 301, Issue 2, 2006, Pages 176-181

  Zhao, Yuan Cong ^a   Xiang, Yong Ze ^a   Pu, Lin ^b   Yang, Meng ^a   Yu, Xiao Qi ^a  

^a SICHUAN UNIVERSITY   (China)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Selective epoxidation; Ruthenium porphyrin; Supported; Unsaturated steroids

Indexed keywords

CATALYSTS; DRUG PRODUCTS; LEACHING; PORPHYRINS; UNSATURATED COMPOUNDS;

Β-SELECTIVE EPOXIDATION; RUTHENIUM PORPHYRIN; SUPPORTED; UNSATURATED STEROIDS;

RUTHENIUM;

EID: 32044436576     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2005.11.025     Document Type: Article

References (42)

1. A.A. Kandutsch, H.W. Chen, and H.J. Heiniger Science 201 1978 498
2. L.L. Smith, and B.H. Johnson Free Radic. Biol. Med. 7 1989 285
3. P.L. Hwang Bio. Essays 13 1991 583
4. T. Muto, J. Umehara, H. Masumori, T. Miura, and M. Kimura Chem. Pharm. Bull. 33 1985 4749
5. G.M. Blackburn, A. Rashid, and M.H. Thompson J. Chem. Soc. Chem. Commun. 1979 420
6. G.P. Raaphorst, E.I. Azzam, R. Langlois, and J.E. Vanlier Biochem. Pharmacol. 36 1987 2369
7. L.L. Smith Cholesterol Autoxidation 1981 Plenum Press New York
8. T.J. Scallen, A.K. Dhar, and E.D. Loughran J. Biol. Chem. 246 1971 3168
9. T. Watable, M. Kanai, M. Isobe, and V. Ozawa J. Biol. Chem. 256 1981 2900
10. A. Bowers, and H.J. Ringold J. Am. Chem. Soc. 80 1958 3091
11. H.J. Ringold, O. Mancera, C. Djerassi, A. Bowers, E. Batres, H. Martinez, E. Necoechea, J.A. Edwards, M. Velasco, C.C. Campillo, and R.I. Dorfman J. Am. Chem. Soc. 80 1958 6464
12. A. Bowers, and H.J. Ringold J. Am. Chem. Soc. 80 1958 4423
13. J.W.L. Bok, J. Chilton, H.G. Kligneman, and G.H.N. Towers Phytochemistry 51 1999 891
14. R. Tschesche, H. Schwang, and G. Legler Tetrahedron 22 1966 1121
15. M. Gamoh, and N. Ikekawa J. Chem. Soc., Perkin Trans. 1 1984 449
16. P. Bovicelli, P. Lupattelli, E. Mincione, T. Prencipe, and R. Curci J. Org. Chem. 57 1992 2182
17. B.A. Marples, J.P. Muxworthy, and K.H. Baggaley Tetrahedron Lett. 32 1991 533
18. G. Cicala, R. Curci, M. Fiorentino, and O. Laricchiuta J. Org. Chem. 47 1982 2670
19. D.P. Michaud, N.T. Nashed, and D.M. Jerina J. Org. Chem. 50 1985 1835
20. T. Muto, J. Umehara, H. Masumori, T. Miura, and M. Kimura Chem. Pharm. Bull. 33 1985 4749
21. G.J. Mathews, and A. Hassner J. Fried J.A. Edwards Organic Reaction in Steroid Chemistry vol. 2 1972 Van Nostrand Reinhold Company New York 2
22. J.C. Marchon, and R. Ramasseul J. Chem. Soc. Chem. Commun. 1988 298
23. J.A.R. Salvador, M.L. Soe Mtlo, and A.S. Campos Tetrahedron Lett. 37 1996 687
24. D. Yang, and G.-S. Jiao Chem. Eur. J. 6 2000 3517
25. Z.-K. Li, X.-M. Wen, M. Li, X.-Q. Yu, M. Yang, and R.-G. Xie Chem. Res. Appl. 15 2003 359
26. C.-P. Du, Z.-K. Li, X.-M. Wen, J. Wu, X.-Q. Yu, M. Yang, and R.-G. Xie J. Mol. Catal. A: Chem. 216 2004 7
27. M. Hirobe, T. Higuchi, and H. Ohtake J. Am. Chem. Soc. 114 1992 10660
28. J.T. Groves, M. Bonchio, T. Carofiglio, and K. Shalyaev J. Am. Chem. Soc. 118 1996 8961
29. A. Berkessel, and M. Frauenkron J. Chem. Soc. Perkin Trans. 1 1997 2265
30. L. Sun, C.-P. Du, J. Qin, J.-S. You, M. Yang, and X.-Q. Yu J. Mol. Catal. A: Chem. 234 2005 29
31. R.J. Rouseau, and R.K. Robins J. Heterocycl. Chem. 2 1965 196
32. C. Gaget, D. Morel, M. Traore, and J. Serpint Analysis 12 1984 386
33. P. Battioni, J.F. Bartoli, D. Mansuy, Y.S. Byun, and T.G. Traylor J. Chem. Soc. Chem. Commun. 1992 1051
34. S.I. Murahashi, T. Maota, and N. Komoiya Tetrahedron Lett. 36 1995 8059
35. A.D. Cross J. Chem. Soc. Chem. Commun. 84 1962 3206
36. X.-Q. Yu, J.-S. Huang, W.-Y. Yu, and C.-M. Che J. Am. Chem. Soc. 122 2000 5337
37. Y. Tsuda, K. Takahashi, T. Yamaguchi, S. Matsui, and T. Komura J. Mol. Catal. A: Chem. 130 1998 285
38. E. Brule, and Y.R. Miguel Tetrahedron Lett. 43 2002 8555
39. O. Nestler, and K. Severin Org. Lett. 3 2001 3907
40. T. Higuchi, and M. Hirobe J. Mol. Catal. A: Chem. 113 1996 403
41. F.S. Vinhado, C.M.C. Prado-Manso, H.C. Sacco, and Y. Iamanoto J. Mol. Catal. A: Chem. 174 2001 279
42. M.D.D. Assis, and J.R.L. Smith J. Chem. Soc. Perkin Trans. 2 1998 2221