Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450: Osmiumporphyrin complex/tert-butyl hydroperoxide system

Journal of Organic Chemistry

Volumn 72, Issue 3, 2007, Pages 823-830

  Iida, Takashi ^a   Ogawa, Shoujiro ^a   Hosoi, Keiji ^a   Makino, Mitsuko ^a   Fujimoto, Yasuo ^a   Goto, Takaaki ^b   Mano, Nariyasu ^b   Goto, Junichi ^b,c   Hofmann, Alan F ^d  

^a NIHON UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY HOSPITAL   (Japan)

^d UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTRANES; OXYFUNCTIONALIZATION; PREGNANES; STEROIDS;

CATALYSIS; CHEMICAL BONDS; COMPLEXATION; DEGRADATION; OSMIUM COMPOUNDS; PEROXIDES; STEREOCHEMISTRY;

LIPIDS;

(5,10,15,20 TETRAMESITYLPORPHYRINATE)OSMIUM CARBONYL COMPLEX; CARBON; CARBONYL DERIVATIVE; CHOLANIC ACID DERIVATIVE; CHOLESTANE DERIVATIVE; CYTOCHROME P450; ESTRANE DERIVATIVE; OSMIUM DERIVATIVE; PORPHYRIN DERIVATIVE; PREGNANE DERIVATIVE; STEROID; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEROID ANALYSIS;

CARBON; CHOLANES; CYTOCHROME P-450 ENZYME SYSTEM; ESTRANES; HYDROXYLATION; MODELS, BIOLOGICAL; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; OSMIUM; OXIDATION-REDUCTION; PORPHYRINS; PREGNANES; STEROIDS; TERT-BUTYLHYDROPEROXIDE;

EID: 33846916688     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061800g     Document Type: Article

References (54)

1. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841.
2. Meunier, B. Chem. Rev. 1992, 92, 1411.
3. Reese, P. B. Steroids 2001, 66, 481.
4. (a) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
5. (b) Ohtake, H.; Higuchi, T.; Hirobe, M. Heterocycles 1995, 40, 867.
6. (c) Higuchi, T.; Satake, C.; Hirobe, M. J. Am. Chem. Soc. 1995, 117, 8879.
7. (d) Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861.
8. (a) Iida, T.; Ogawa, S.; Shiraishi, K.; Kakiyama, G.; Goto, T.; Mano, N.; Goto, J. ARKIVOC 2003, viii, 171.
9. (b) Iida, T.; Ogawa, S.; Miyata, S.; Goto, T.; Mano, N.; Goto, J.; Nambara, T. Lipids 2004, 39, 873.
10. (c) Ogawa, S.; Iida, T.; Goto, T.; Mano, N.; Goto, J.; Nambara, T. Org. Biomol. Chem. 2004, 2, 1013.
11. Zhang, R.; Yu. W.-Y.; Che, C-H. Tetrahedron: Asymmetry 2005, 16, 3520.
12. (a) Paulson, D. R.; Ullman, R.; Sloane, R. B.; Closs, G. L. J. Chem. Soc., Chem. Commun. 1974, 186.
13. (b) Mansuy, D.; Bartoli, J.-F.; Chottard, J.-C.; Lange, M. Angew. Chem., Int. Ed. Engl. 1980, 19, 909.
14. (c) Chauhan, S. M. S.; Kandadai, A. S.; Jain, N.; Kumar, A. Chem. Pharm. Bull. 2003, 51, 1345.
15. (d) Constantino, L.; Iley, J. Org. Biomol. Chem. 2004, 2, 1894.
16. (e) Rebelo, S. L. H.; Pereira, M. M.; Simões, M. M. Q.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. J. Catal. 2005, 234, 76.
17. (a) Battioni, P.; Renaud, J. P.; Bartoni, J. F.; Reina-Artiles, M.; Fort, M.; Mansuy, D. J. Am. Chem. Soc. 1988, 110, 8462.
18. (b) Collman, J. P.; Tanaka, H.; Membre, R. T.; Brauman, J. I. J. Am. Chem. Soc. 1990, 112, 3689.
19. (c) Banfi, S.; Maiocchi, A.; Moggi, A.; Montanari, F.; Quici, S. J. Chem. Soc., Chem. Commun. 1990, 1794.
20. (d) Breslow, R.; Huang, Y.; Zhang, X.; Yang, J. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 11156.
21. (e) Gross, Z.; Simkhovich, L.; Galili, N. Chem. Commun. 1999, 599.
22. (f) Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531.
23. (g) Belvedere, S.; Breslow, R. Bioorg. Chem. 2001, 29, 321.
24. (h) Collman, J. P.; Zeng, L.; Decréau, R. A. Chem. Commun. 2003, 2974.
25. (i) Smith, J. R. L.; Iamamoto, Y.; Vinhalo, F. S. J. Mol. Catal. A: Chem. 2006, 252, 23.
26. Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
27. (a) Che, C.-M.; Chung, W.-C. J. Chem. Soc., Chem. Commun. 1986, 386.
28. (b) Gross, Z.; Mahammed, A. J. Mol. Catal. A: Chem. 1999, 142, 367.
29. (c) Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M. J. Am. Chem. Soc. 2001, 123, 4843.
30. Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545.
31. Nappa, M. J.; Tolman, C. A. Inorg. Chem. 1985, 24, 4711.
32. Kuroda, Y.; Hiroshige, T.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1990, 1594.
33. Brown, D. S.; Marples, B. A.; Muxworthy, J. P.; Baggaley, K. H. J. Chem. Res., Synop. 1992, 28.
34. Modica, E.; Bombieri, G.; Colombo, D.; Marchini, N.; Ronchetti, F.; Scala, A.; Toma, L. Eur. J. Org. Chem. 2003, 2964.
35. (a) Blunt, J. W. Aust. J. Chem. 1975, 28, 1017.
36. (b) Eggert, H.; VanAntwerp, C. L.; Bhacca, N. S.; Djerassi, C. J. Org. Chem. 1976, 41, 71.
37. Iida, T.; Shiraishi, K.; Ogawa, S.; Goto, T.; Mano, N.; Goto, J.; Nambara, T. Lipids 2003, 38, 281.
38. Cerrè, C.; Hofmann, A. F.; Schteingart, C. D.; Jia, W.; Maltby, D. Tetrahedron 1997, 53, 435.
39. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T. J. Chem. Soc., Perkin Trans. 1 2001, 2229.
40. Arnone, A.; Cavicchioli, M.; Montanari, V.; Resnati, G. J. Org. Chem. 1994, 59, 5511.
41. Bégué, J.-P. J. Org. Chem. 1982, 47, 4268.
42. Rotmann, A.; Mazur, Y. J. Am. Chem. Soc. 1972, 94, 6228.
43. Ruddock, P. L.; Williams, D. J.; Reese, P. B. Steroids 2004, 69, 193.
44. Oliveto, E. P. In Organic Reactions in Steroid Chemistry: Synthesis and Degradation of the Pregnane Side-Chain; Fried, J., Edwards, J. A., Eds.; Van Nostrand Reinhold: New York, 1971; Vol. II, pp 127-236.
45. Fukuyama, Y.; Kubo, M.; Minami, H.; Yuasa, H.; Matsuo, A.; Fujii, T.; Morisaki, M.; Harada, K. Chem. Pharm. Bull. 2005, 53, 72-80.
46. VanAntwerp, C. L.; Eggert, H.; Meakins, G. D.; Miners, J. O.; Djerassi, C. J. Org. Chem. 1977, 42, 789.
47. Iida, T.; Momose, T.; Chang, F. C.; Goto, J.; Nambara, T. Chem. Pharm. Bull. 1989, 37, 3323.
48. Groves, J. T. Inorg. Biochem. 2006, 100, 434.
49. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Margurettaz, A. M. J. Org. Chem. 1987, 52, 827.
50. Che, C.-M.; Poon, C.-K.; Chung, W.-C.; Gray. H. B Inorg. Chem. 1985, 24, 1277.
51. Cardwell, H. M. E.; Cornforth, J. W.; Duff, S. R.; Holtermann, H.; Robinson, R. J. Chem. Soc. 1953, 361.
52. Issidorides, C. H.; Fieser, M.; Fieser, L. F. J. Am. Chem. Soc. 1960, 82, 2002.
53. Dalton, F.; McDougall, J. I.; Meakins, G. D. J. Chem. Soc. 1963, 4068.
54. David, N. K.; Harold, C. T.; Christal, D.; Karen, A. W.; Kelvin, E. S.; Shahid, L.; Robert, W. P. H. J. Chem. Soc., Perkin Trans. 2 1990, 1567.