The Stereochemistry of Epoxidation of Δ⁵-Steroids with Sodium Perborate and Potassium Permanganate†

Abstract

Sodium perborate, with potassium permanganate as a catalyst, has been shown to be a novel reagent for the epoxidation of steroidal 5-enes with the attack occurring predominantly on the β-face.

References

1. K. D. Bingham, T. M. Blaiklock, R. C. B. Coleman and G. D. Meakins, J. Chem. Soc. C, 1970, 2330.
2. J. R. Hanson and A. Truneh, J. Chem. Soc., Perkin Trans. 1, 1988, 2001.
3. L. R. Galagovsky and E. G. Gras, J. Chem. Res. (S), 1993, 137.
4. M. S. Syamala, J. Das, S. Baskaran and S. Chandrasekaran, J. Org. Chem., 1992, 57, 1928.
5. J. R. Hanson, P. B. Hitchcock, M. D. Liman, S. Nagaratnam and R. Manickavasagar, J. Chem. Res., 1995, (S) 200; (M) 1335.
6. E. J. Parish, H. Li and S. Li, Synth. Commun., 1995, 25, 927.
7. J. R. Hanson, S. Nagaratnam and J. Stevens, J. Chem. Res. (S), 1996, 102.
8. E. J. Parish and S. Li, J. Chem. Res. (S), 1996, 288.
9. J. A. R. Salvador, M. L. Sae Melo and A. S. Campos Neves, Tetrahedron Lett., 1996, 37, 687.
10. M. Ehrenstein and M. T. Decker, J. Org. Chem., 1940, 5, 544.
11. A. D. Cross, J. Am. Chem. Soc., 1962, 84, 3206.
12. For a review see: A. McKillop and W. R. Sanderson, Tetrahedron, 1995, 51, 6145.
13. H. R. Nace and A. L. Rieger, J. Org. Chem., 1970, 35, 3846.
14. P. N. Chakravarty and R. Levin, J. Am. Chem. Soc., 1942, 64, 2317.
15. L. Ruzicka and A. C. Muhr, Helv. Chim. Acta, 1944, 27, 503.
16. A. M. Bell, A. D. Boul, E. Jones, G. D. Meakins and A. L. Wilkins, J. Chem. Soc., Perkin Trans. 1, 1975, 1364.
17. M. Akhtar and D. H. R. Barton, J. Am. Chem. Soc., 1964, 86, 1528.
18. J. Joska, J. Fajkos and F. Sorm, Coll. Czech. Chem. Commun., 1963, 28, 82.