Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Novel 4'α-Phenyl and 5'α-Methyl Branched Carbocyclic Nucleosides

  • Oh, Chang-Hyun (Medicinal Chemistry Research Center, Korea Institute of Science and Technology) ;
  • Hong, Joon-Hee (College of Pharmacy, Chosun University)
  • Published : 2005.10.20
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Abstract

This paper describes the racemic and stereoselective synthetic route for a novel 4'$\alpha$-phenyl and 6'$\alpha$-methyl doubly branched carbocyclic nucleosides from an acyclic 2-hydroxy acetophenone. The installation of phenyl group at the 4'-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement. The stereoselective introduction of a methyl group in the 6'$\alpha$-position was accomplished by Felkin-Anh controlled alkylation. Bis-vinyl 11 compound was successfully cyclized using a Grubbs’ catalyst II to desired carbocycles. The natural bases (adenine and cytosine) were efficiently coupled using a Pd(0) catalyst. Although all the synthesized compounds were examined for their activity against several viruses such as HIV-1, HSV-1, HSV-2 and HCMV, only cytosine analogues 17 exhibited weak antiviral activity against HCMV.

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References

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