Cardiotonic steroids are a broad group of natural products that vary in chemical functionality and biological activity. Two steroids of interest are oleandrin and beaumontoside. Oleandrin is currently obtained through extraction from <i>Nerium oleander</i> and beaumontoside is not commercially available, but similar in structure to oleandrin providing potential as a therapeutic. Oleandrin is of interest for its anti-viral properties including treating flu like symptoms and reducing SARS-CoV-2 levels by 3000-fold in golden hamsters. Our group is interested in oleandrin’s use in treating Alzheimer’s disease using its ability to cross the blood brain barrier and reducing cellular prion protein levels. We developed the first synthesis of oleandrin and beaumontoside for therapeutic investigation and accessibility through synthetic means. These studies are, to our knowledge, the first direct comparison of 2-deoxyglycosylation methods in natural product synthesis. Future studies will allow for derivatives to be synthesized in hopes of a suitable treatment for Alzheimer’s disease.

Synthesis of 2-deoxyglycoside containing cardiotonic steroids oleandrin and beaumontoside

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