Autoxidation of isotachysterol under atmospheric oxygen in the dark at ambient temperature produces two new epoxides: (3S,5R)- and (3S,5S)-5,10-epoxy-isotachy sterols.
(a) FeldmanD., GlorieuxF.H., and PikeJ.W., Eds., Vitamine D, Academic Press, San Diego, 1997; (b) HavingaE., Experientia, 1973, 15, 1181.
2.
(a) HorstR.L., and ReinhardtT. A., in Vitamine D, FeldmanD., GlorieuxF. H., and PikeJ. W., Eds., Academic Press, San Diego, 1997, pp. 13–31; (b) H. Reichel, H. R. Koeffler and A. W. Norman, New Engl. J. Med., 1989, 320, 980.
3.
(a) TianW.-S., HeL.-W., and WangC., in Progress in Steroid Chemistry, ZhouW.-S., and ZhuangZ.-P., Eds., Science Press, Beijing, 2002, pp. 204–230; (b) B. Yeung and P. Vouros, Mass Spectr. Rev., 1995, 14, 179; (c) T. Fujishima, K. Konno, K. Nakagawa, M. Kurobe, T. Okano and H. Takayama, Bioorg. Med. Chem., 2000, 8, 123.
4.
DeLucaH.F., SchnoesH. K., and TanakaY., U. S. Patent 4 229 395, 1980.
5.
NakayamaK., YamadaS., and TakayamaH., J. Org. Chem., 1984, 49, 1537.
6.
(a) KingJ.M., and MinD. B., J. Food. Sci., 1998, 63, 31; (b) S. Yamada, K. Nakayama, H. Takayama, A. Itai and Y. Iitaka, J. Org. Chem., 1983, 48, 3477.
