Stereoselective Synthetic Routes to Iminosugars: A Divergent Approach Utilizing a Common Multifunctional Chiral Scaffold

Dedicated to Professor H. Ila on her 80^th birthday.

Abstract

Starting from an l-serine-derived multifunctional aminobutenolide as a common chiral building block, stereoselective synthetic routes to representative examples of di-, tri-, and tetrahydroxylated iminosugars have been developed. Key steps in the synthetic routes involved an intramolecular aminolysis protocol to form the azaheterocyclic core, and functionalization of a resident alkene moiety towards installation of the desired substituents at the various positions of the piperidine ring. The strategy and the approach described are expected to provide flexible synthetic routes to various iminosugar scaffolds of structural and medicinal chemical significance.

Key words

l-serine - chiral aminobutenolide - stereoselective synthesis - iminosugars - glycosidase inhibitors

Publication History

Received: 06 May 2024

Accepted after revision: 26 June 2024

Accepted Manuscript online:
26 June 2024

Article published online:
22 July 2024

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