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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 9
BKCSDE 30(9)
September 20, 2009 

Selective Synthesis of 1'(α),2'(β)-C-Dimethyl Carbocyclic Adenosine Analogue as Potential anti-HCV Agent
Hua Li, Wonjae Lee, Jin Cheol Yoo, Joon Hee Hong*
Mitsunobu reaction, Dihydroxylation, Carbodine, anti-HCV agents
As a part of an ongoing effort to discover inhibitors of the Hepatitis C Virus RNA replication, we describe here the first synthetic route of 1'(α),2'(β)-C-dimethyl carbocyclic adenine analogue. The key intermediate cyclopentenyl alcohol 8(α) was prepared from aldehyde 4 using ring-closing metathesis (RCM) as a key reaction. Coupling of 8(α) with nucleosidic base via the regioselective Mitsunobu reaction followed by stereoselective dihydoxylation and deprotection afforded the target carbocyclic adenine analogue 12.
2039 - 2042
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