The reduction of the bulky enone 1 derived from ergosterol was performed in non-aqueous media without and with proton donor. A fairly stable anion radical was obtained and characterized. When 1 was reduced in the presence of an efficient proton donor (benzoic acid, trifluoroacetic acid) saturation of the double bond was achieved with reasonable yield. The overall process as a function of experimental conditions is discussed.
[Tsantrizos, Youla S.; Folkins, Patricia L.; Britten, James F.; Harpp, David N.; Ogilvie, Kelvin K. Canadian Journal of Chemistry, 1992 , vol. 70, p. 158 - 164]
