Reaction of RuO4 with carbon-carbon double bonds. Part 8. 1 Reaction of 7,8-didehydrocholesteryl acetate and cholesteryl acetate with RuO4 and OsO4. A comparative view

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 1998, Pages 737-743

  Albarella, Laura ^a   Lasalvia, Maria ^a   Piccialli, Vincenzo ^a   Sica, Donato ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001436628     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700294g     Document Type: Article

References (36)

1. For part 7 see ref. 7.
2. V. Piccialli, D. Sica and D. Smaldone, Tetrahedron Lett., 1994, 35, 7093.
3. 4, in Oxidation in Organic Chemistry, ed. W. S. Trahanovsky, Academic Press, New York, 1973, vol. 5, part B, ch. 4.
4. A. Migliuolo, V. Piccialli and D. Sica, Tetrahedron, 1991, 47, 7937.
5. V. Piccialli, D. Smaldone and D. Sica, Tetrahedron, 1993, 49, 4211.
6. G. Notaro, V. Piccialli, D. Smaldone and D. Sica, Tetrahedron, 1994, 50, 4835.
7. L. Albarella, V. Piccialli, D. Smaldone and D. Sica, J. Chem. Res., 1996, (S) 400; (M) 2442.
8. L. Albarella, V. Piccialli, D. Smaldone and D. Sica, J. Chem. Res., 1996, (S) 400; (M) 2442.
9. K. B. Sharpless and K. Akashi, J. Am. Chem. Soc., 1976, 98, 1986.
10. T. K. M. Shing, E. K. W. Tarn, V. W-F. Tai, I. H. F. Chung and Q. Jiang, Chem. Eur. J., 1996, 2, 5057.
11. R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. Iwao Ojima, VCH, Weinheim, 1993, pp. 227-272.
12. (a) P. O. Norrby, C. H. KoIb and B. K. Sharpless, Organometallics, 1994, 13, 344;
13. (b) P. O. Norrby, C. H. Kolb and B. K. Sharpless, J. Am. Chem. Soc., 1996, 118, 35.
14. K. A. Jorgensen and R. Hoffmann, J. Am. Chem. Soc., 1986, 108, 1867.
15. (a) K. Tomioka, M. Nakajima and K. Koga, J. Am. Chem. Soc., 1987, 198, 6213;
16. (b) K. Tomioka, M. Nakajima, Y. Itaka and K. Koga, Tetrahedron Lett., 1988, 29, 573;
17. (c) K. Tomioka, M. Nakajima and K. Koga, J. Chem. Soc., Chem. Commun., 1989, 1921;
18. (d) K. Tomioka, M. Nakajima and K. Koga, Tetrahedron Lett., 1990, 31, 1741.
19. (a) E. J. Corey, P. D. Jardine, S. Virgil, P.-W. Yuen and D. Connel, J. Am. Chem. Soc., 1989, 111, 9243;
20. (b) E. J. Corey and G. I. Lotto, Tetrahedron Lett., 1990, 31, 2665;
21. (c) E. J. Corey, M. C. Noe and S. Sarshar, J. Am. Chem. Soc., 1993, 115, 3828;
22. (d) E. J. Corey and M. C. Noe, J. Am. Chem. Soc., 1993, 115, 12 579;
23. (e) E. J. Corey, M. C. Noe and S. Sarshar, Tetrahedron Lett., 1994, 35, 2861;
24. (f) E. J. Corey, M. C. Noe and M. J. Grogan, Tetrahedron Lett., 1994, 35, 6427;
25. (g) E. J. Corey, A. Guzman-Perez and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 12 109;
26. (h) E. J. Corey, A. Guzman-Perez and M. C. Noe, J. Am. Chem. Soc., 1995, 117, 10 805;
27. (i) E. J. Corey, A. Guzman-Perez and M. C. Noe, J. Am. Chem. Soc., 1995, 117, 10 817;
28. (j) E. J. Corey and M. C. Noe, J. Am. Chem. Soc., 1996, 118, 319;
29. (k) E. J. Corey, M. C. Noe and M. J. Grogan, Tetrahedron Lett., 1996, 37, 4899.
30. (a) U. Pidun, C. Boehme and G. Frenking, Angew. Chem., Int. Ed. Engl., 1996, 35, 2817;
31. (b) A. Veldkamp and G. Frenking, J. Am. Chem. Soc., 1994, 116, 4937.
32. -1).
33. J. K. H. Bridgemann, P. C. Cherry, A. S. Clegg, J. M. Evans, E. R. H. Jones, A. Kasal, V. Kumar, G. D. Meakins, Y. Morisawa, E. E. Richards and P. D. Woodgate, J. Chem. Soc. C, 1970, 250.
34. In all the ruthenate and osmate esters that we have so far studied, the carbons geminal to the metal resonated in the range 80-100 ppm.
35. 4 oxidation of a-pinene we hypothesized that ruthenium(VI) diesters possess a structure similar to that of osmium(VI) diesters in which the metal adopts a square-based pyramidal five-coordination.
36. 3β-Acetoxy-5-hydroxy-5α-cholestan-6-one and 5α-cholestane-3β,5, 6α-triol 3-acetate, the final oxidation products of cholesteryl acetate, were both present in the filtrate of the reaction mixture; their yields were as previously described (ref. 5).