Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Selective Synthesis of 1'(α),2'(β)-C-Dimethyl Carbocyclic Adenosine Analogue as Potential anti-HCV Agent

  • Li, Hua (BK21-Project Team, College of Pharmacy, Chosun University) ;
  • Lee, Won-Jae (BK21-Project Team, College of Pharmacy, Chosun University) ;
  • Yoo, Jin-Cheol (BK21-Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK21-Project Team, College of Pharmacy, Chosun University)
  • Published : 2009.09.20
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Abstract

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'($\alpha$),2'($\beta$)-C-dimethyl carbocyclic adenine analogue. The key intermediate cyclopentenyl alcohol 8($\alpha$) was prepared from aldehyde 4 using ring-closing metathesis (RCM) as a key reaction. Coupling of 8($\alpha$) with nucleosidic base via the regioselective Mitsunobu reaction followed by stereoselective dihydoxylation and deprotection afforded the target carbocyclic adenine analogue 12.

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References

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