An enantioselective and modular platform for C4ʹ-modified nucleoside analogue synthesis enabled by intramolecular trans-acetalizations

Thirupathi Nuligonda, Gautam Kumar, Jason W. Wang, Dinithi Rajapaksha, Ismael A. Elayan, Ramiz Demir, Neil J. Meanwell, Sherrie F. Wang, Lara K. Mahal, Alex Brown and Michael W. Meanwell ()
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Thirupathi Nuligonda: University of Alberta
Gautam Kumar: University of Alberta
Jason W. Wang: University of Alberta
Dinithi Rajapaksha: University of Alberta
Ismael A. Elayan: University of Alberta
Ramiz Demir: University of Alberta
Neil J. Meanwell: University of Alberta
Sherrie F. Wang: North Island College
Lara K. Mahal: University of Alberta
Alex Brown: University of Alberta
Michael W. Meanwell: University of Alberta

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract C4ʹ-modified nucleoside analogues continue to attract global attention for their use in antiviral drug development and oligonucleotide-based therapeutics. However, current approaches to C4ʹ-modified nucleoside analogues still involve lengthy (9–16 steps), non-modular routes that are unamenable to library synthesis. Towards addressing the challenges associated with their syntheses, we report a modular 5-step process to a diverse collection of C4ʹ-modified nucleoside analogues through a sequence of intramolecular trans-acetalizations of readily assembled polyhydroxylated frameworks. Overall, the 2–3 fold reduction in step-count compares favorably to even recently reported biocatalytic approaches and should ultimately enable new opportunities in drug design around this popular chemotype.

Date: 2024
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DOI: 10.1038/s41467-024-51520-5

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