Aminocyclopentanols - Potential glycosidase inhibitors

Recently several aminocyclopentanols having the aminogroup adjacent to a carbon sidechain, proved to be potent and anomer-selective glycosidase inhibitors.1 The bicyclic lactone 1, which has been synthesised in our group from sugar-derived starting materials, was found to be suited for further functionalisation with amino and hydroxy functionalities.2 Various ways of functionalising 1 have now been investigated. Thus compound 3 was obtained by an Overman rearrangement of 2, and 4 was synthesised via an epoxide formed from 1, followed by opening with NaN3. Having introduced a nitrogen functionality in the desired position, 3 and 4 were easily converted into the aminocyclopentanols 5 and 6. Other aminocyclopentanols, which have been synthesised from 1, will be presented, and their activities and specificities as glycosidase inhibitors will be discussed.