RuCl3-TBHP mediated allylic oxidation of Δ8(9) lanosterol derivatives

Tetrahedron Letters

Volumn 52, Issue 45, 2011, Pages 6007-6010

  Shingate, Bapurao B ^a,b   Hazra, Braja G ^a,b   Salunke, Deepak B ^a,b   Pore, Vandana S ^a,b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

Allylic oxidation; Oxygenated steroids; Ruthenium chloride; Steroidal ketones; t Butyl hydroperoxide

Indexed keywords

7,11 DIENONE; DELTA 8(9) LANOSTEROL DERIVATIVE; KETONE; LANOSTEROL DERIVATIVE; RUTHENIUM; RUTHENIUM CHLORIDE; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION;

EID: 80053605020     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.166     Document Type: Article

References (47)

1. A.A. Kanduutsch, H.W. Chen, and H.-J. Heiniger Science 201 1978 498 501
2. E.J. Parish, V.B.B. Nanduri, H.H. Kohl, and F.R. Taylor Lipids 21 1986 27 30
3. L.L. Smith Free Radical Biol. Med. 11 1991 47 61
4. P. Nordmann, M. Diez-Ibanez, M. Chessebeuf-Padieu, B. Luu, G. Mack, and M. Mersel Cell Biol. Toxicol. 5 1989 261 270
5. P.L. Hwang Bioassays 13 1991 538 589
6. M.M. Christ, Y.H. Ji, C. Moog, X. Pannecoucke, G. Schmitt, P. Bischoff, and B. Luu Anticancer Res. 11 1991 359 364
7. M. Werthle, D. Bochelen, M. Adamczyk, A. Kupferberg, P. Poulet, J. Chambron, P. Lutz, A. Privat, and M. Mersel Cancer Res. 54 1994 998 1003
8. P.L. Bischoff, V. Holl, D. Coelho, P. Dufour, B. Luu, and D. Weltin Curr. Med. Chem. 7 2000 693 713
9. B.A. Janowski, P.J. Willy, T.R. Devi, J.R. Falck, and D.J. Mangelsdorf Nature 383 1996 728 731
10. J.M. Lehmann, S.A. Kliewer, L.B. Moore, T.A. Smith-Oliver, B.B. Oliver, J.L. Su, S.S. Sundseth, D.A. Winegar, D.E. Blanchard, T.A. Spencer, and T.M. Willson J. Biol. Chem. 272 1997 3137 3140
11. W.D. Nes Biochim. Biophys. Acta 1529 2000 63 88
12. S.R. Panini, R.C. Sexton, A.K. Gupta, and E.J. Parish J. Lipid Res. 27 1986 1190 1204
13. G. Schroepfer J. Physiol. Rev. 80 2000 361 554
14. S.-K. Chung, C.H. Ryoo, H.-W. Yang, J.-Y. Shim, and H.I. Kang Korean J. Med. Chem. 8 1998 10 13
15. S.-K. Chung, C.H. Ryoo, H.-W. Yang, J.-Y. Shim, and H.I. Kang Korean J. Med. Chem. 8 1998 14 17
16. S.-K. Chung, C.H. Ryoo, H.-W. Yang, J.-Y. Shim, M.G. Kang, K.W. Lee, and H.I. Kang Tetrahedron 54 1998 15899 15914
17. P.A. Leone, J. Redburn, J.N.A. Hooper, and R.J. Quinn J. Nat. Prod. 63 2000 694 697
18. T.-S. Wu, L.S. Shi, and S.-C. Kuo J. Nat. Prod. 64 2001 1121 1122
19. L.-Y. Wang, N.-L. Wang, X.-S. Yao, S. Miyata, and S. Kitanaka J. Nat. Prod. 66 2003 630 633
20. J.-J. Gao, N. Nakamura, B.-S. Min, A. Hirakawa, F. Zuo, and M. Hattori Chem. Pharm. Bull. 52 2004 688 695
21. H.-L. Yang, G.-H. Chen, and Y.-Q. Li Eur. J. Med. Chem. 40 2005 972 976
22. A.J. Pearson, Y.S. Chen, G.R. Han, S.H. Hsu, and T. Ray J. Chem. Soc., Perkin Trans. 1 1985 267 273
23. J. Muzart Tetrahedron Lett. 28 1987 4665 4668
24. J. Muzart Synth. Commun. 19 1989 2061 2067
25. Y. Ishi, K. Nakayama, M. Takeno, S. Satoshi, T. Iwahama, and Y. Nishiyama J. Org. Chem. 60 1995 3934 3935
26. R.A. Miller, W. Li, and G.R. Humphrey Tetrahedron Lett. 37 1996 3429 3432
27. J.A.R. Salvador, M.L. SaeMelo, and A.S.C. Neves Tetrahedron Lett. 38 1997 119 122
28. J.A.R. Salvador, and J.H. Clark Chem. Commun. 2001 33 34
29. M. Jurado-Gonzalez, A.C. Sullivan, and J.R.H. Wilson Tetrahedron Lett. 44 2003 4283 4286
30. P. Marwah, A. Marwah, and H.A. Lardy Green Chem. 5 2004 570 577
31. J.A.R. Salvador, and S.M. Silvestre Tetrahedron Lett. 46 2005 2581 2584
32. T.K.M. Shing, Y.-Y. Yeung, and P.L. Su Org. Lett. 8 2006 3149 3151
33. M.A. Fousteris, A.I. Koutsourea, S.S. Nikolaropoulos, A. Riahi, and J. Muzart J. Mol. Catal. A: Chem. 250 2006 70 74
34. J.A.R. Salvador, S.M. Silvestre, and V.M. Moreira Curr. Org. Chem. 17 2006 2227 2257
35. S.M. Silvestre, and J.A.R. Salvador Tetrahedron 63 2007 2439 2445
36. H. Choi, and M.P. Doyle Org. Lett. 9 2007 5349 5352
37. E.C. McLaughlin, H. Choi, K. Wang, G. Chiou, and M.P. Doyle J. Org. Chem. 74 2009 730 738
38. Y. Li, X. Wu, T.B. Lee, E.K. Isbell, E.J. Parish, and E.V. Gorden J. Org. Chem. 75 2010 1807 1810
39. K. Takahashi, K. Usami, T. Takahashi, T. Okada, and M. Morisaki Chem. Pharm. Bull. 35 1987 3467 3469
40. W.J. Rodewald, and J.J. Jagodzinski Pol. J. Chem. 53 1979 1203 1210
41. W.J. Rodewald, and J.J. Jagodzinski Pol. J. Chem. 55 1981 1751 1757
42. H.-S. Kim, B.-S. Choi, K.-C. Kwon, S.-O. Lee, H.J. Kwak, and C.H. Lee Bioorg. Med. Chem. 8 2000 2059 2065
43. F. Launay, A. Roucoux, and H. Patin Tetrahedron Lett. 39 1998 1353 1356
44. G. Rothenberg, L. Feldberg, H. Wiener, and Y. Sasson J. Chem. Soc., Perkin Trans. 2 1998 2429 2434
45. E.S. Arsenou, A.I. Koutsourea, M.A. Fousteris, and S.S. Nikolaropoulos Steroids 68 2003 407 414
46. B.A. Allal, L. Firdoussi, S. Allaoud, A. Karim, Y. Costanet, and A. Mortreux J. Mol. Catal. A: Chem. 200 2003 177 184
47. E. Modica, G. Bombieri, D. Colombo, N. Marchini, F. Ronchetti, A. Scala, and L. Toma Eur. J. Org. Chem. 2003 2964 2971