Stereoselective synthesis of (+)-1-deoxyaltronojirimycin

Abstract

A stereocontrolled, facile and high-yield approach for producing (+)-altroDNJ, has been developed starting from the inexpensive commercial cis 2-butene-1,4-diol. The Sharpless epoxidation and a subsequent dihydroxylation were used for the introduction of all stereocenters; finally the ring closure in basic conditions afforded the piperidine heterocycle.