Reactions of the ketone derived from (±)-3,4,5-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol: preparation of racemic derivatives of epi-inositol and of 4-C-methyl-epi- [(±)-iso-laminitol] and 4-C-methyl-myo-inositol [(±)-laminitol]

Abstract Oxidation of (±)-3,4,5-tri- O -benzyl-1,2- O -isopropylidene- myo -inositol with the pyridine-SO 3 complex in methyl sulfoxide gave the ketone which was reduced with sodium borohydride to give almost exclusively the corresponding epi -inositol derivative. Reaction of the ketone with diazomethane gave an epoxide which was reduced with lithium aluminium hydride to give a 4- C -methyl- myo -inositol derivative and reaction of the ketone with methyl magnesium iodide gave the isomeric 4- C -methyl- epi -inositol derivative.