Indolyl N??glycoside analogs were obtained by a two??step sequence via indole N?? thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N??thioamide. The use of 10: 1 toluene: THF as solvent is important in favoring N??over C 3??acylation. Treatment of the ω??hydroxythioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N??( ...