Selective oxidation of the double bonds in the 4-phenyl-1,2,4-triazoline-3,5-dione diels-alder adduct of ergosterol acetate.
Methods for oxidations at the 6(7)- and 22(23)-double bonds in the phenyltriazoline adduct of ergosterol acetate (I) are described. KMnO4 and OsO4 were found to react with the 6(7)-double bond to yield the 6,7-glycol and osmate ester, respectively. Other reagents (I2/AgOAc, H2O2, m-chloroperbenzoic acid, HCO3H) formed either isomeric epoxides or glycols with the 22(23)-double bond, with the latter two reagents giving their products in quite high yields.
D055598:Chemical Phenomena; D002621:Chemistry; D004852:Epoxy Compounds; D004875:Ergosterol / Q000032:analysis*; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D011196:Potassium Permanganate; D014466:Ultraviolet Rays
D004852:Epoxy Compounds; D007202:Indicators and Reagents; D011196:Potassium Permanganate; D004875:Ergosterol