Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction

Steroids

Volumn 75, Issue 10, 2010, Pages 721-725

  Astná, Eva ^a   Erný, Ivan ^a   Pouzar, Vladimír ^a   Chodounská, Hana ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Borohydride reduction; Stereoselectivity; Steroid; Synthesis

Indexed keywords

ALCOHOL; CERIUM; OXOSTEROID; SAMARIUM; SODIUM BOROHYDRIDE; BORANE DERIVATIVE; KETONE; STEROID;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LUCHE REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

BOROHYDRIDES; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM; STEROIDS;

EID: 77954312690     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2010.04.010     Document Type: Article

References (32)

1. J.L. Luche Lanthanides in organic chemistry. 1. Selective 1,2 reduction of conjugated ketones J Am Chem Soc 100 1978 2226 2227
2. A.L. Gemal, and J.L. Luche Lanthanoides in organic synthesis. 6. The reduction by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects J Am Chem Soc 18 1981 5454 5466
3. J.M. Brunel, C. Loncle, N. Vidal, M. Dherbomez, and Y. Letourneux Synthesis and antifungal activity of oxygenated cholesterol derivatives Steroids 70 2005 907 912
4. S. Fouace, L. El kihel, M. Dherbomez, and Y. Letourneux Stereoselective synthesis of 7α- and 7β-aminocholestanol as potent fungicidal drugs Bioorg Med Chem Lett 11 2001 3011 3014
5. D.C. Labaree, R.M. Hoyte, L.V. Nazareth, N.L. Weigel, and R.B. Hochberg 7α-iodo and 7α-fluoro steroids as androgen receptor-mediated imaging agents J Med Chem 42 1999 2021 2034
6. R. Micková Reduction of 12-oxo derivatives of some bile-acids Collect Czech Chem Commun 50 1985 1239 1243
7. 3 reagent Bull Chim Soc Fr 133 1996 801 803
8. O. Mancera, H.J. Ringold, C. Djerassi, G. Rosenkrantz, and F. Sondheimer Steroids. XLIII. A ten step conversion of progesterone to cortisone. The differential reduction of pregnane-3,20-diones with sodium borohydride J Org Chem 75 1953 1286 1290
9. R.T. Li, and Y. Sato D-Homoannulation of 5α-pregnane-3β, 20β-diol 3-acetate with phosphorus pentabromide J Org Chem 33 1968 3632 3635
10. L.N. Monsalve, M.Y. Machado Rada, A.A. Ghini, and A. Baldessari An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one Tetrahedron 64 2008 1721 1730
11. F.B. Hirschmann, D.M. Kautz, S.S. Deshmane, and H. Hirschmann Formolysis of 3β-acetoxy-5α-pregnan-20α-yl p-toluenesulfonate Tetrahedron 27 1971 2041 2053
12. M. Hossain, and D.N. Kirk 18-Substituted steroids. Part 4. A chemical synthesis of 3α,18,21-trihydroxy-5β-pregnan-20-one 18,20-hemiacetal (18-hydroxy-tetrahydro-DOC) Steroids 34 1979 677 680
13. J.W. Ralls, F.J. Saunders, A.L. Raymond, and B. Riegel Two reduction products from the adrenal perfusion of pregnane-3,20-dione J Biol Chem 210 1954 709 712
14. E.P. Oliveto, T. Clayton, and E.B. Hershberg 11-Oxygenated steroids. III. The preparation of 11β-hydroxy pregnanes J Am Chem Soc 75 1953 486 488
15. H.L. Herzog, M.A. Jevnik, and E.B. Hershberg 11-Oxygenated steroids. II. The reduction of 11-carbonyl to 11α-hydroxyl in the etiocholane series J Am Chem Soc 75 1953 269 272
16. J. Xue, P. Liu, Y. Pan, and Z. Guo A total synthesis of OSW-1 J Org Chem 73 2008 157 161
17. K.J. Pawlak, G. Zhang, and J.P. Wiebe Membrane 5α-pregnane-3,20- dione (5αP) receptors in MCF-7 and MCF-10. Breast cancer cells are up-regulated by estradiol and 5αP and down-regulated by the progesterone metabolites, 3α-dihydroprogesterone and 20α-dihydroprogesterone, with associated changes in cell proliferation and detachment J Steroid Biochem Mol Biol 97 2005 278 288
18. K. Heusler, and J. Kalvoda Photolysis of nitrites (Barton reaction) J. Fried, J.A. Edwards, Organic reactions in steroid chemistry vol. II 1972 Van Nostrand New York 253 256
19. G. Göndös, G. Dombi, and J.C. Orr A new chiral director for the highly diastereoselective borane reduction of steroid-20-ones Monatsh Chem 131 2000 1055 1059
20. W.E. Fristad, T.R. Bailey, and L.A. Paquette Silanes in organic synthesis. 9. Enesilylation as a method for 1,2-carbonyl migration within ketones and for conversion to 1,2-transposed allylic alcohols J Org Chem 45 1980 3028 3037
21. J. Libman, M. Sprechert, and Y. Mazur Reactions of acid anhydrides - I. Reactions of ketones with trichloroacetic anhydride Tetrahedron 25 1969 1679 1698
22. M. Ishige, M. Shiota, and F. Suzuki Study on the preparation of 3α-hydroxy-5α-cholesta-6-one and 7-one by stereoselective catalytic hydrogenation Can J Chem 54 1976 2581 2583
23. S. Takatsuto, and N. Ikekawa Synthesis of 5α-cholestan-6-one derivatives with some substituents at the C-1, C-2, or C-3 position Chem Pharm Bull 35 1987 986 995
24. H.J. Liu, and I.S. Han Direct conversion of silyl ethers into carbonyl compounds with Jones reagent in the presence of potassium fluoride Synth Commun 15 1985 759 764
25. B. Voigt, J. Schmidt, and G. Adam Synthesis of 24-epiteasterone, 24-epityphasterol and their B-homo-6a-oxalactones from ergosterol Tetrahedron 52 1996 1997 2004
26. R.J. Batten, A.J. Dixon, R.J.K. Taylor, and R.F. Newton A new method for removing the t-butyldimethylsilyl protecting group Synthesis 1980 234 236
27. H. Chodounská, and A. Kasal Epalons: synthesis of 3α,7α-dihydroxy-5α-pregnan-20-one Collect Czech Chem Commun 63 1998 1543 1548
28. K. Heusler, J. Kalvoda, G. Anner, and A. Wettstein Über Reaktionen von Alkoxyradikalen. Epimerisierungen in der Steroid Reihe. Über Steroide, 194. Mitteilung Helv Chim Acta 46 1963 352 364
29. T. Sawaya, and M. Kimura Autoxidation of cholanic acid in the presence of ferrous ions Chem Pharm Bull 31 1983 1207 1212
30. I. Ghilezan, E.R.H. Jones, G.D. Meakins, and J.O. Miners Preparation of 3β-hydroxy-5α-androstan-16-one J Chem Soc Perkin Trans 1 1976 1350 1351
31. Commercial product from Steraloids, m.p. 168-170 °C.
32. Commercial product from Steraloids, m.p. 140-150 °C.