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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 5
BKCSDE 29(5)
May 20, 2008 

An Efficient Synthesis of 4'-Vinylated Carbocyclic Nucleoside Analogues via Two Directional Ring-closing Metathesis
Hua Li, Joon Hee Hong*
Vinylated carbocyclic nucleoside, Antiviral agents, Weinreb amide
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 (EC50 = 10.2 μM).
993 - 997
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