A GENERAL SYNTHETIC STRATEGY TOWARD AMINOCYCLOPENTITOL GLYCOSIDASE INHIBITORS - APPLICATION OF PALLADIUM CATALYSIS TO THE SYNTHESIS OF ALLOSAMIZOLINE AND MANNOSTATIN-A

A general strategy for the synthesis of aminocyclopentitol glycosidase inhibitors has been applied to the synthesis of allosamizoline and mannostatin A. These cyclic pseudosugars are members of a growing family of highly potent and selective glycosidase inhibitors. A palladium-catalyzed ionization/cyclization reaction for preparing oxazolidinones from meso-alkenediols forms the cornerstone for this approach toward the synthesis of highly functionalized cyclopentane rings.