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

Srinath Pashikanti; Apurba Datta

doi:10.1055/a-2353-1618

Synthesis, Table of Contents

Synthesis 2025; 57(01): 138-146
DOI: 10.1055/a-2353-1618

paper

Special Topic Dedicated to Prof. H. Ila

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

Srinath Pashikanti

^aDepartment of Biomedical and Pharmaceutical Sciences, College of Pharmacy, Idaho State University, 921 S. 8th Avenue, Stop 8288, Pocatello, ID 83209, USA

,

Apurba Datta ∗

^bDepartment of Medicinal Chemistry, University of Kansas, Room 1083 Del Shankel Structural Biology Center, 2034 Becker Drive, Lawrence, KS 66047, USA

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Abstract

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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

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References

References
1 The studies described here are based on previously unpublished results from Srinath Pashikanti’s doctoral dissertation titled A serine-derived butenolide as a versatile chiral building block: Applications in the synthesis of natural and nature-like compounds of biological significance as submitted to the University of Kansas, Lawrence, KS, USA (accessed Jul 12, 2024): https://kuscholarworks.ku.edu/handle/1808/21638

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