Studies on the construction of abutasterone-type and 24-epi-abutasterone- type side chains employing asymmetric dihydroxylation of (E)-20(22),24- cholestadiene

Tetrahedron Asymmetry

Volumn 16, Issue 23, 2005, Pages 3913-3918

  Tsubuki, Masayoshi ^a   Iwabuchi, Kazuo ^a   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

20,22,24,25 TETRAHYDROXY 6BETA METHOXY 3ALPHA,5 CYCLO 5ALPHA CHOLESTANE; 20,24 CHOLESTADIENE; 20,24 DIHYDROXY 6BETA METHOXY 3ALPHA,5 CYCLO 25 HOMO 5ALPHA CHOLANO 25,22 LACTONE; 24 EPIABUTASTERONE; 24,25 DIHYDROXY 6BETA METHOXY 3ALPHA,5 CYCLO 5ALPHA CHOLEST 20(22) ENE; CHOLESTANE DERIVATIVE; ECDYSTEROID; HYDROXY 20 CHOLESTANE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIHYDROXYLATION; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 28644437354     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.11.001     Document Type: Article

References (42)

1. For recent reviews, see: L. Dinan Phytochemistry 57 2001 325 339
2. L. Dinan, T. Savchenko, and P. Whiting Cell. Mol. Life Sci. 58 2001 1121 1132
3. K. Nakanishi Steroids 57 1992 649 657
4. For recent reviews, see: M. Bathori, and Z. Pongracz Curr. Med. Chem. 12 2005 153 172
5. R. Lafont, and L. Dinan J. Insect Sci. 3 2003 1 30
6. For recent reviews, see: R. Lafont, C. Dauphin-Villemant, J.T. Warren, and H. Rees Compr. Mol. Insect Sci. 3 2005 125 195
7. L. Dinan Bioactive Nat. Prod. 29 2003 3 71
8. M.L.B. Pinheiro, W. Wolter Filho, A.I. Da Rocha, B. Porter, and E. Wenkert Phytochemistry 22 1983 2320 2321
9. A. Suksamrarn, N. Promrangsan, B. Chitkul, S. Homvisasevongsa, and A. Sirikate Phytochemistry 45 1997 1149 1152
10. A. Suksamrarn, N. Promrangsan, and A. Jintasirikul Phytochemistry 53 2000 921 924
11. J. Coll, N. Reixach, F. Sanchez-Baeza, J. Casas, and F. Camps Tetrahedron 50 1994 7247 7252
12. U. Baltaev, Y.V. Rashkes, and N.K. Abubakirov Khim. Prir. Soedin. 4 1985 522 525
13. T. Takemoto, Y. Hikino, T. Arai, M. Kawahara, C. Konno, S. Arihara, and H. Hikino Chem. Pharm. Bull. 15 1967 1816
14. T. Kametani, M. Tsubuki, H. Furuyama, and T. Honda J. Chem. Soc., Chem. Commun. 1984 375 376
15. T. Kametani, M. Tsubuki, K. Higurashi, and T. Honda J. Org. Chem. 51 1986 2932 2939
16. T. Honda, K. Keino, and M. Tsubuki J. Chem. Soc., Chem. Commun. 1990 650 651
17. M. Tsubuki, K. Keino, and T. Honda J. Chem. Soc., Perkin Trans. 1 1992 2643 2649
18. M. Tsubuki, K. Kanai, K. Keino, N. Kakinuma, and T. Honda J. Org. Chem. 57 1992 2930 2934
19. M. Tsubuki, H. Takada, T. Katoh, S. Miki, and T. Honda Tetrahedron 46 1996 14515 14532
20. M. Tsubuki, A. Ohinata, T. Tanaka, K. Takahashi, and T. Honda Tetrahedron 61 2005 1095 1100
21. For recent reviews, see: H.C. Kolb, and K.B. Sharpless M. Beller C. Bolm Transition Metals for Organic Synthesis Vol. 2 2004 Wiley-VCH Weinheim 275 298
22. H. Becker, and K.B. Sharpless T. Katsuki Asymmetric Oxidation Reactions 2001 Oxford University Press Oxford 81 104
23. H.C. Kolb, M.S. VanNieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483 2547
24. Suksamrarn et al. reported the synthesis of 24-epi-abutasterone by the asymmetric dihydroxylation of stachysteorne C. B.-E. Yingyongnarongkul, and A. Suksamrarn Tetrahedron 54 1998 2795 2800
25. K. Bannai, M. Morisaki, and N. Ikekawa J. Chem. Soc., Perkin Trans. 1 1976 2116 2120
26. M. Morisaki, S. Sato, and N. Ikekawa Chem. Pharm. Bull. 25 1977 2576 2583
27. C.-Y. Byon, and M. Gut J. Org. Chem. 41 1976 3716 3722
28. M.F. Ansell, and D.A. Thomas J. Chem. Soc. 1961 539 542
29. G. Büchi, and J.E. Powell Jr. J. Am. Chem. Soc. 92 1970 3126 3133
30. W. Jiang, M.J. Fuertes, and W.D. Wulff Tetrahedron 56 2000 2183 2194
31. J.P. Schmidt, M. Piraux, and J.F. Pilette J. Org. Chem. 40 1975 1586 1588
32. S.R. Schow, and T.C. McMorris J. Org. Chem. 44 1979 3760 3765
33. R.B. Bates, R.H. Carnighan, R.O. Rakutis, and J.H. Schauble Chem. Ind. 1962 1020 1021
34. B.M. Trost Acc. Chem. Res. 3 1970 120 130
35. See, for example: J. Cossy, F. Pradaux, and S. BouzBouz Org. Lett. 3 2001 2233 2235
36. K. Miyashita, M. Ikejiri, H. Kawasaki, S. Maemura, and T. Imanishi Chem. Commun. 2002 742 743
37. Y.K. Reddy, and J.R. Falck Org. Lett. 4 2002 969 971
38. E. Vedejs J. Am. Chem. Soc. 96 1974 5944 5946
39. E. Vedejs, D.A. Engler, and J.E. Telschow J. Org. Chem. 43 1978 188 196
40. E.J. Corey, and M.J. Grogan Tetrahedron Lett. 39 1998 9351 9354
41. 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. Wilson J. Biol. Chem. 272 1997 3137 3140
42. B.A. Janowski, P.J. Willey, T.R. Devi, J.R. Falck, and D.J. Mangelsdorf Nature 383 1996 728 731