• Title/Summary/Keyword: Vinylated carbocyclic nucleoside

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An Efficient Synthesis of 4'-Vinylated Carbocyclic Nucleoside Analogues via Two Directional Ring-closing Metathesis

  • Li, Hua;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.29 no.5
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    • pp.993-997
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    • 2008
  • Two directional ring-closing metathesis (RCM) was applied successfully to the synthesis of 4'-vinylated carbocyclic nucleoside analogues from the trivinyl intermediate 12, which was readily made using a sequential Claisen rearrangement and ring-closing metathesis (RCM) starting from Weinreb amide 5. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the guanine analogue 20 have moderate anti-HIV activity in the MT-4 cell line ($EC_{50}$ = 10.2 $\mu$ M).