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Synthesis
DOI: 10.1055/a-2353-1618
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Stereoselective Synthetic Routes to Iminosugars: A Divergent Approach Utilizing a Common Multifunctional Chiral Scaffold

Srinath Pashikanti
1   Department of Biomedical and Pharmaceutical Sciences, Idaho State University College of Pharmacy, Pocatello, United States (Ringgold ID: RIN15470)
,
Apurba Datta 
2   Department of Medicinal Chemistry, The University of Kansas, Lawrence, United States
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Starting from an L-serine-derived multifunctional aminobutenolide as a common chiral building block, stereoselective synthetic routes to representative examples of di-, tri-, and tetra-hydroxylated 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.



Publication History

Received: 06 May 2024

Accepted after revision: 26 June 2024

Accepted Manuscript online:
26 June 2024

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