Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 6966-6971Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02555
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Funding
- Studienstiftung des deutschen Volkes (Promotionsstipendium)
- Fonds der Chemischen Industrie (Promotionsstipendium)
- Helmholtz-Alberta initiative for infectious disease research (HAI-IDR)
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The Simmons-Smith-Furukawa reaction was used to generate 4'/5'-spirocyclopropanated uridine analogs from electron-rich exocyclic enol esters. During synthesis, the native hydroxylation pattern of the nucleoside is preserved and offers the possibility for a late stage 5'-phosphorylation at the spirocyclopropanol moiety. All synthesized spirocyclopropanated uridine derivatives, including the corresponding 5'-monophosphate (cpUMP), were evaluated with respect to their antiviral activity in an HRSV assay showing moderate, but promising activity.
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