The Synthesis of Cyclophellitol-Aziridine and Its Configurational and Functional Isomers.

Cyclophellitol and cyclophellitol-aziridine are potent, mechanism-based and irreversible retaining β-glucosidase inhibitors. We have become interested in these configurational β-glucoside analogues as they proved to be a highly suitable starting point for the development of activity-based glycosidase probes. In this review, we provide an overview of the cyclophellitol-aziridine synthesis reported in the literature. Two conceptually different strategies for the introduction of the aziridine moiety have been used, one starting from the inverted epoxide and one with intramolecular iodocyclisation from a homo-allylic alcohol as the key step. These are discussed in this microreview, and their application in the synthesis of configurational and functional cyclophellitol-aziridine isomers is presented as well. [ABSTRACT FROM AUTHOR]