A PRACTICAL AND DIVERGENT WAY TO TRIHYDROXYLATED PYRROLIDINE DERIVATIVES AS POTENTIAL GLYCOSIDASE INHIBITORS VIA STEREOSELECTIVE INTERMOLECULAR CIS-AMIDOALKYLATIONS

A practical and divergent way from the common tartrimide 1 to trihydroxylated pyrrolidines 2a-h as potential glycosidase inhibitors has been developed. cis-Amidoalkylations on the acyliminium intermediate 5 of the corresponding TBS-protected tartaric imide with the tin reagents afforded the desired structures 6a-c in good yields and high selectivities. In this reaction the adjacent OTBS group controls the stereoselectivity in the presence of a Lewis acid MgBr2. Transformations to each desired pyrrolidine could be achieved via efficient methods including selective protection, functionalization of the unsaturated bonds, and reduction of the amide group.