Dual-Face Nucleoside Scaffold Featuring a Stereogenic All-Carbon Quaternary Center. Intramolecular Silicon Tethered Group-Transfer Reaction

The design of a novel nucleoside scaffold that exhibits an all-carbon quaternary center is reported. This allows for both α- and β-anomers of a given 2′-deoxy-2′,2′-difluoro nucleoside analog (NA) to have potential biological activity. Using an intramolecular atom-transfer reaction, an all-carbon qu...

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Bibliographic Details
Published in:Organic letters 2014-11, Vol.16 (21), p.5698-5701
Main Authors: Tambutet, Guillaume, Becerril-Jiménez, Fabiola, Dostie, Starr, Simard, Ryan, Prévost, Michel, Mochirian, Philippe, Guindon, Yvan
Format: Article
Language:English
Subjects:
Catalysis
Molecular Structure
Nucleosides - chemistry
Silicon - chemistry
Stereoisomerism
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Summary:The design of a novel nucleoside scaffold that exhibits an all-carbon quaternary center is reported. This allows for both α- and β-anomers of a given 2′-deoxy-2′,2′-difluoro nucleoside analog (NA) to have potential biological activity. Using an intramolecular atom-transfer reaction, an all-carbon quaternary center was obtained without the use of heavy metals and/or harsh conditions. The chemistry developed is efficient, easily scalable and leads to novel libraries of molecules.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502777r