New synthesis of (+)-and (–)-nojirimycin from myo-inositol
Abstract
A report of a new synthesis of nojirimycin (1a), as well as its antipode (1b), from optically active seven-membered hemiacetal lactones (2a,b) derived from myo-inositol by a five step reaction; the hydrogen sulphite adduct of (1b) shows high inhibitory activity against β-glucosidase and α-mannosidase, being almost comparable to that of mannojirimycin.