Expeditious synthesis of aminocyclopentitols from D-ribose via intramolecular nitrone cycloaddition

Abstract

The synthesis of 4α-aminocyclopentane-1α, 2β,3β-triol (a key-intermediate in the preparation of carbocyclic nucleosides) and its N-substituted derivatives, has been achieved by the Intramolecular nitrone cycloadditions of a γ-unsaturated aldehyde, easily accessible from D-ribose, followed by reductive N–O bond cleavage in the resulting bicyclic oxazanes.