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]

Article abstract of DOI:10.1016/S0008-6215(96)00330-8

Oxidation of (±)-3,4,5-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol with the pyridine-SO₃, 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.