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
a   Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, Idaho State University, 921 S. 8th Avenue, Stop 8288, Pocatello, ID 83209, USA
,
Apurba Datta
b   Department of Medicinal Chemistry, University of Kansas, Room 1083 Del Shankel Structural Biology Center, 2034 Becker Drive, Lawrence, KS 66047, USA
› Author Affiliations


Dedicated to Professor H. Ila on her 80th 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.

Supporting Information



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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