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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 12
BKCSDE 30(12)
December 20, 2009 

Selective Ring-opening Fluorination of Epoxide: An Efficient Synthesis of 2'-C-Fluoro-2'-C-methyl Carbocyclic Nucleosides
Lian Jin Liu, Si Wouk Kim, Wonjae Lee, Joon Hee Hong*
Fluorohydrin, Carbocyclic nucleoside, Anti-HCV agent, Mitsunobu reaction
An efficient synthetic route of novel 2′(α)-C-fluoro-2′(β)-C-methyl carbocyclic nucleoside analogues is described. The key fluorinated intermediate 7 was prepared from the epoxide intermediate 5 via selective ring-opening of epoxide. Coupling of 7 with nucleosidic bases under the Mitsunobu reactions followed by deprotection afforded the target carbocyclic nucleoside analogues. The synthesized compounds were evaluated as inhibitors of the hepatitis C virus (HCV) in Huh-7 cell line in vitro.
2989 - 2992
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