A simple diastereoselective access to amino- and hydrazinocyclopentitols is described. The key step involves a cationic rearrangement of a meso bicyclic hydrazine, followed by two successive stereoselective hydroxylations. Both racemic compounds are micromolar alpha-mannosidase (Jack bean) inhibitors.
Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av de l'Observatoire, 75270 Paris Cedex 06, France.