The solid-phase oxidation of steroidal alkenes with potassium permanganate and metal salts

Journal of Chemical Research

Volumn , Issue 8, 2004, Pages 513-516

  Salvador, Jorge A R ^a   Hanson, James R ^b  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

Epoxidation introduction; Metal salts; Potassium permanganate; Steroidal alkenes

Indexed keywords

ALKENE; CHOLESTANE DERIVATIVE; CHOLESTANOL; CHOLESTEROL; METAL; OLEIC ACID; PERMANGANATE POTASSIUM; STEROID; TESTOSTERONE;

CATALYSIS; CHEMICAL STRUCTURE; EPOXIDATION; OXIDATION; PH; REACTION ANALYSIS; REVIEW; SOLUBILITY; STEREOCHEMISTRY;

EID: 7644227114     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/0308234042564027     Document Type: Review

References (43)

1. A.J. Fatiadi, Synthesis, 1987, 85; L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, Chichester, 1995, vol.6, p.4274
2. A.J. Fatiadi, Synthesis, 1987, 85; L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, Chichester, 1995, vol.6, p.4274
3. see, for example, J.E. Coleman, C. Ricciuti and D. Swern, J. Am., Chem. Soc., 1956, 78, 5342.
4. G.M. Robinson and R. Robinson, J. Chem. Soc., 1925, 127, 175.
5. A. Lapworth and E.N. Mottram, J. Chem. Soc., 1925, 127, 1628.
6. B. Ellis and V. Petrow, J. Chem. Soc., 1939, 1078; R.E. Marker and E. Rohmann, J. Am. Chem. Soc., 1940, 62, 516.
7. B. Ellis and V. Petrow, J. Chem. Soc., 1939, 1078; R.E. Marker and E. Rohmann, J. Am. Chem. Soc., 1940, 62, 516.
8. M. Fieser, A. Quilico, A. Nickon, W.E. Rosen, E.J. Tarlton and L.F. Fieser, J. Am. Chem. Soc., 1953, 75, 4066; see also M. Anastasia, A. Fiecchi and A. Scala, Tetrahedron Lett., 1979, 3323.
9. M. Fieser, A. Quilico, A. Nickon, W.E. Rosen, E.J. Tarlton and L.F. Fieser, J. Am. Chem. Soc., 1953, 75, 4066; see also M. Anastasia, A. Fiecchi and A. Scala, Tetrahedron Lett., 1979, 3323.
10. H. Singh and D. Paul, J. Chem. Soc. Perkin Trans.l, 1974, 1475; A.P. King and R.E. Benson, Org. Synth. Coll. Vol.VI, 1988, 690.
11. H. Singh and D. Paul, J. Chem. Soc. Perkin Trans.l, 1974, 1475; A.P. King and R.E. Benson, Org. Synth. Coll. Vol.VI, 1988, 690.
12. H.R. Nace and A.L. Rieger, J. Org. Chem., 1970, 35, 3846.
13. G.W. Gokel and H.D. Durst, Synthesis, 1976, 168; Angew. Chem. Int. Ed. Engl. 1979, 18, 787
14. G.W. Gokel and H.D. Durst, Synthesis, 1976, 168; Angew. Chem. Int. Ed. Engl. 1979, 18, 787
15. V. Bushen, R. Rathore and S. Chandrasekaran, Synthesis, 1984, 431.
16. D.J. Sam and H.F. Simmons, J. Am. Chem. Soc., 1972, 94, 4024; 1974, 96, 2252.
17. D.J. Sam and H.F. Simmons, J. Am. Chem. Soc., 1972, 94, 4024; 1974, 96, 2252.
18. K.B. Wiberg and K.A. Saegebarth, J. Am. Chem. Soc., 1957, 79, 2822.
19. S. Lai and D.G. Lee, Tetrahedron, 2002, 58, 9879.
20. S.L. Regen and C.J. Koteel, J. Am. Chem. Soc., 1977, 99, 3837.
21. H.J. Clark and D.G. Cork, J. Chem. Soc., Chem. Commun. 1982, 635.
22. F.M. Menger and C. Lee, J. Org. Chem., 1979, 44, 3446.
23. C.W. Jefford and Y. Wang, J. Chem. Soc. Chem. Commun., 1988, 634.
24. N.A. Noureldin, W.B. McConnell and D.G. Lee, Canad. J. Chem., 1984, 62, 2113.
25. D.G. Lee and N.A. Noureldin, J. Am. Chem. Soc., 1983, 105, 3188.
26. S. Baskaran, J. Das and S. Chandrasekaran, J. Org. Chem., 1989, 54, 5182.
27. S. Baskaran, I. Islam, P.S. Vankar and S. Chandrasekaran. J. Chem. Soc. Chem. Commun, 1990, 1670.
28. M.S. Syamala, J. Das, S. Baskaran and S. Chandrasekaran, J. Org. Chem., 1992, 57, 1928.
29. A.K. Rappe and W.A. Goodard, J. Chem. Soc., 1982, 104, 448, and 3287.
30. K.D. Bingham, T.M. Blaiklok, R.C.B. Coleman and G.D. Meakins, J. Chem. Soc. (C). 1970, 2330.
31. J.R. Hanson, N. Terry and C. Uyanik, J. Chem. Research (S) 1998, 50.
32. E. Glotter, Natural Product Reports, 1991, 8, 415.
33. J.R. Hanson, P.B. Hitchcock, M.D. Liman, S. Nagaratnam and R. Manickavasagar, J. Chem. Research (S), 1995, 220; (M) 1335.
34. J.R. Hanson, P.B. Hitchcock, M.D. Liman, S. Nagaratnam and R. Manickavasagar, J. Chem. Research (S), 1995, 220; (M) 1335.
35. E.J. Parish, H. Li and S. Li, Synthetic Communications, 1995, 25, 927
36. J.R. Hanson, S. Nagaratnam and J. Stevens, J. Chem. Research (S), 1996, 102.
37. J.A.R. Salvador, M.L. SaeMelo and A.S. Campos Neves, Tetrahedron Lett., 1996, 37, 687
38. J.A.R. Salvador, J.R. Hanson and P.B. Hitchcock, unpublished work.
39. J.A.R. Salvador and J.R. Hanson, J. Chem. Research (S) 2002, 576.
40. E.J. Parish and S. Li, J. Org. Chem., 1996, 61, 5665.
41. E.J. Parish and S. Li, J. Chem. Research (S), 1996, 288.
42. J.R. Hanson, P.B. Hitchcock and S. Nagaratnam J. Chem. Research (S), 1999, 22; (M), 319.
43. J.R. Hanson, P.B. Hitchcock and S. Nagaratnam J. Chem. Research (S), 1999, 22; (M), 319.