Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides

  • Published : 2004.12.20
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Abstract

The stereoselective synthesis 4′,6′-dually branched carbocyclic nucleosides was accomplished in this study. The introduction of a methyl group in the 6′$({\alpha})$-position was accomplished by Felkin-Anh controlled alkylation. The construction of the required 4′$({\alpha})$-quaternary carbon was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited good antiviral activity against the HCMV.

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References

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