Synthesis of 1-deoxy-L-gulonojirimycin and 1-deoxy-L-talonojirimycin

De novo synthesis of noncompetitive glycosidase inhibitors L-gulo-DNJ and L-talo-DNJ has been achieved in 9-10 steps starting from Garner's aldehyde. Key to the success of this procedure was the construction of the 2,3-unsaturated piperidine 14, which syn dihydroxylation under Kishi's and Donohoe's conditions led to the desired iminosugars. (c) 2009 Elsevier Ltd. All rights reserved.