Optimal TBHP allylic oxidation of Δ5 - Steroids catalyzed by dirhodium caprolactamate

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5349-5352

  Choi, Hojae ^a   Doyle, Michael P ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(PHENYL)DIRHODIUM(III) CAPROLACTAMATE; CAPROLACTAM; DRUG DERIVATIVE; ORGANOMETALLIC COMPOUND; RHODIUM; STEROID; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

CAPROLACTAM; CATALYSIS; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RHODIUM; STEROIDS; TERT-BUTYLHYDROPEROXIDE;

EID: 38349093052     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7025284     Document Type: Article

References (44)

1. Reviews: (a) Parish, E. J.; Kizito, S. A.; Qiu, Z. Lipids 2004, 801.
2. (b) Arsenou, E. S.; Fousteris, M. A.; Koutsourea, A. I.; Nikolaropoulos, S. S. Mini Rev. Med. Chem. 2003, 3, 557.
3. (c) Smith, L. Lipids 1996, 31, 453.
4. (d) Peng, S.-K.; Morin, R. J. The Biological Effects of Cholesterol Oxides; CRC Press: Boca Raton, FL, 1992.
5. (a) Lee, J. W.; Fuda, H.; Javitt, N. B.; Strott, C. A.; Rodriguez, I. R. Exp. Eye Res. 2006, 83, 465.
6. (b) Berthier, A.; Lemaire-Ewing, S.; Prunet, C.; Monier, S.; Athias, A.; Bessade, G.; Paisde Barros, J.-P.; Laubriet, A.; Gambert, P.; Lizard, G.; Nacel, D. Cell Death Differ. 2004, 11, 897.
7. (c) Deckert, V.; Duverneuil, L.; Poupon, S.; Monier, S.; de Guern, N.; Lizard, G.; Masson, D.; Lagrost, L. Brit. J. Pharm. 2002, 137, 655.
8. (d) Steffen, Y.; Wiswedel, I.; Peter, D.; Schewe, T.; Sies, H. Free Radicals Biol. Med. 2006, 41, 1139.
9. (e) Javitt, N. B. Curr. Opin. Lipidol. 2007, 18, 283.
10. (a) Rabjohn, N. Org. React. 1976, 24, 261.
11. (b) Crich, D.; Zou, Y. Org. Lett. 2004, 6, 775.
12. (a) Hua, Z.; Carcache, D. A.; Tian, Y.; Li, Y.-M.; Danishefsky, S. J. J. Org. Chem. 2005, 70, 9849.
13. (b) Bora, U.; Chaudhuri, M. K.; Dey, D.; Kalita, D.; Kharmawphlang, W.; Mandai, G. C. Tetrahedron 2001, 57, 2445.
14. (c) Kasal, A. Tetrahedron 2000, 56, 3559.
15. (d) Li, D.; Spencer, T. A. Steroids 2000, 65, 529.
16. (e) Labaree, D.; Hoyte, R. M.: Hochberg, R. B. Steroids 1998, 63, 454.
17. (f) Parish, E. J.; Wei, T.-Y. Synth. Commun. 1987, 17, 1227.
18. (g) Dauben, W. G.; Fullertyon, D. S. J. Org. Chem. 1971, 36, 3277.
19. Silvestre, S. M.; Salvador, J. A. R. Tetrahedron 2007, 63, 2439.
20. Fousteris, M. A.; Koutsourea, A. I.; Nikolaropoulos, S. S.; Riahi, A.; Muzart, J. J. Mol. Catal. A: Chem. 2006, 250, 70.
21. Shing, T. K. M.; Yeung, Y. Y.; Su, P. L. Org. Lett. 2006, 8, 3149.
22. Salvador, J. A. R.; Silvestre, S. M. Tetrahedron Lett. 2005, 46, 2581.
23. Arsenou, E. S.; Koutsourea, A. I.; Fousteris, M. A.; Nikolaropoulos, S. S. Steroids 2003, 68, 407.
24. Salvador, J. A. R.; Clark, J. H. Chem. Commun. 2001, 33.
25. (a) Baptistella, L. H.; Sousa, I. M. O.; Gushikem, Y.; Aleixo, A. M. Tetrahedron Lett. 1999, 40, 2595.
26. (b) Muzart, J. Synth. Commun. 1989, 19, 2061.
27. Miller, R. A.; Li, W.; Humphrey, G. R. Tetrahedron Lett. 1996, 37, 3429.
28. Catino, J.; Forslund, R. E.; Doyle, M. P. J. Am. Chem. Soc 2004, 126, 13622.
29. 1'5-12
30. (a) Akihisa, T.; Matsumoto, T.; Sakamaki, H.; Take, M.; Ichinohe, Y. Bull. Chem. Soc Jpn. 1986, 59, 680.
31. (b) Dang, H.-S.; Davies, A. G.; Davison, I. G. E.; Schiesser, C. H. J. Org. Chem. 1990, 55, 1432.
32. (c) Ponce, M. A.; Ramirez, J. A.; Galagovsky, L. R.; Gros, E. G.; Erra-Balsells, R. J. Chem. Soc., Perkin Trans. 2 2000, 2351.
33. 4 were with 0.27 M TBHP (5 molar equiv).
34. Salvador, J. A. R.; Melo, M. L. S.; Neves. A. S. C. Tetrahedron. Lett. 1997, 38, 119.
35. (a) Nagiev, T. M. Coherent Synchronized Oxidation Reactions by Hydrogen Peroxide; Elsevier Science, Ltd.: Amsterdam, 2006.
36. (b) Modern Oxidation Methods; Bäckvall, J., Ed., Wiley-VCH: New York, 2004.
37. (a) Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc 2001, 123, 469.
38. (b) MacFaul, P. A.; Arends, I. W. C. E.; Ingold, K. U.; Wayner, D. D. M. J. Chem. Soc., Perkin Trans. 2 1997, 135.
39. Bravo, A.; Bjorsvik, H.-R.; Fontana, F.; Liguori, L.; Minisci, F. J. Org. Chem. 1997, 62, 3849.
40. Yu, J.-Q.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 3232.
41. Chavez, F. A.; Mascharak, P. K. Acc. Chem. Res. 2000, 33, 539.
42. Bozzelli, J. W.; Sheng, C. J. Chem. Phys. A 2002. 106, 1113.
43. 4+.
44. Miyamoto, S.; Martinez, G. R.; Medeiros, M. H. G.; Di Mascio, P. J. Am. Chem. Soc. 2003, 125, 6172.