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DOI: 10.1055/a-2353-1618
Stereoselective Synthetic Routes to Iminosugars: A Divergent Approach Utilizing a Common Multifunctional Chiral Scaffold
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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.
Key words
l-serine - chiral aminobutenolide - stereoselective synthesis - iminosugars - glycosidase inhibitorsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2353-1618. Included are copies of 1H NMR and 13C NMR data of all new compounds synthesized.
- 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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For representative previous syntheses, see: