Iminosugars from α,β-epoxyamides. Part 2: Synthetic approach to hydroxylated pyrrolidine and azepane derivatives

This paper describes a new synthetic route towards hydroxylated pyrrolidines and azepane derivatives starting from chiral epoxyamides. The alternate transformations on a ribose derivative α,β-epoxyamide permit the construction of five or seven member rings leading to different precursors of homoiminosugars.