A complete synthesis of an N-spirofused iminosugar from L-xylose; a potential cholinesterase inhibitor for treatment of Alzheimer’s disease

Abstract

In this bachelor’s project we present a complete synthesis of an N-spirofused iminosugar II with a stable positive charge on the spirocyclic nitrogen atom that together with the hydroxyl groups are expected to establish interactions with the residues in the active gorge of the acetylcholinesterase. Compound II was successfully synthesized through seven steps from commercially available L-xylose at an overall yield of 3%. This was done through the strategy of initiating an SN2 cyclisation on pyrrolidine I, thereby creating the N-spirofused bicyclic iminosugar, before finally removing the protection groups.

In this bachelor’s project we present a complete synthesis of an N-spirofused iminosugar II with a stable positive charge on the spirocyclic nitrogen atom that together with the hydroxyl groups are expected to establish interactions with the residues in the active gorge of the acetylcholinesterase. Compound II was successfully synthesized through seven steps from commercially available L-xylose at an overall yield of 3%. This was done through the strategy of initiating an SN2 cyclisation on pyrrolidine I, thereby creating the N-spirofused bicyclic iminosugar, before finally removing the protection groups.