Collect. Czech. Chem. Commun. 2001, 66, 1764-1776
https://doi.org/10.1135/cccc20011764

Radical Oxidation of 17-Functionalized 14α-Hydroxy Steroids

Vladimir A. Khripacha,*, Vladimir N. Zhabinskiia, Anna I. Kotyatkinaa, Galina P. Fandoa, Yuliya Y. Zhiburtovicha, Alexander S. Lyakhova, Alla A. Govorovaa, Marinus B. Groenb, Jaap van der Louwb and Aede de Grootc

a Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str. 5/2, 220141 Minsk, Belarus
b Scientific Development Group, N. V. Organon, P.O. Box 20, 5340 BH Oss, Netherlands
c Wageningen University, Laboratory of Organic Chemistry, Dreijenplein 8, 6703 HB Wageningen, Netherlands

References

1. Mihailović M. L., Lorenc L., Gašić M., Rosić M., Melera A., Stefanović M.: Tetrahedron 1966, 22, 2345. <https://doi.org/10.1016/S0040-4020(01)82154-2>
2. Balasubramanian V., Robinson C. H.: Tetrahedron Lett. 1981, 22, 501. <https://doi.org/10.1016/S0040-4039(01)90139-X>
3. Mez H.-C., Rist G., Ermer O., Lorenc L., Kalvoda J., Mihailović M. L.: Helv. Chim. Acta 1976, 59, 1273. <https://doi.org/10.1002/hlca.19760590430>
4. Fuhrer H., Lorenc L., Pavlović V., Rihs G., Rist G., Kalvoda J., Mihailović M. L.: Helv. Chim. Acta 1979, 62, 1770. <https://doi.org/10.1002/hlca.19790620610>
5. Covey D. F.: J. Am. Chem. Soc. 1976, 98, 5039. <https://doi.org/10.1021/ja00432a067>
6. Smith A. G., Brooks C. J. W.: Biochem. J. 1977, 167, 121. <https://doi.org/10.1042/bj1670121>
7. Penning T. M., Covey D. F., Talalay P.: J. Biol. Chem. 1981, 256, 6842.
8. Thacker J. D., Bordner J., Bumgardner C.: Phytochemistry 1990, 29, 2965. <https://doi.org/10.1016/0031-9422(90)87116-C>
9. Kirson I., Zaretskii V. I.: J. Chem. Soc., Perkin Trans. 1 1976, 1244. <https://doi.org/10.1039/p19760001244>
10. Anner G., Kalvoda J. (Ciba Ltd.): U.S. 3 470 240; Chem. Abstr. 1966, 65, 775.
11. Bjelaković M. S., Lorenc L. B., Pavlović V. D., Michailović M. L., Tinant B., Declercq J.-P., Kalvoda J.: Helv. Chim. Acta 1999, 82, 707. <https://doi.org/10.1002/(SICI)1522-2675(19990505)82:5<707::AID-HLCA707>3.0.CO;2-O>
12. Altomare A., Burla M. C., Camalli M., Cascarano G., Giacovazzo C., Guagliardi A., Moliterni A. G. G., Polidori G., Spagna R.: J. Appl. Crystallogr. 1999, 32, 115. <https://doi.org/10.1107/S0021889898007717>
13. Sheldrick G. M.: Program for Crystal Structure Refinement. University of Göttingen, Göttingen 1997.
14. Mamlok L.: Bull. Soc. Chim. Fr. 1967, 3827.
15. Rosenthal D., Lefler C. F., Wall M. E.: Tetrahedron 1981, 23, 3583. <https://doi.org/10.1016/0040-4020(67)80005-X>