LETTER A Synthesis of a Trihydroxylated Aminoazepane from D-Glucitol by an

Abstract: Transformation of D-glucitol into its 1,6-diazido deriva-tive allowed its conversion into the polyhydroxylated amino-azepane ring in a one-pot reaction using Ph3P and H2O. Key words: azepanes, 1-deoxynojirimycin, iminosugars, aziridine Polyhydroxylated piperidine derivatives are very interest-ing synthetic targets due to their potent and diverse bio-logical activities, related to their inhibition of glycosidases.1 These compounds are considered to be imi-nosugars because they have the capacity to mimic carbo-hydrate structures and have thus found applications in the treatment of diabetes and other metabolic diseases,2 in ob-structing microbial infection,3 and as antiviral agents, in particular against the human immunodeficiency virus (HIV).4 1-Deoxynojirimycin (DNJ, 1, Figure 1), a potent naturally occurring glycosidase inhibitor, is an example o