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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 25, Number 12
BKCSDE 25(12)
December 20, 2004 

Stereoselective Synthesis and Antiviral Activity of Novel 4′( α)-Hydroxymethyl and 6′( α)-Methyl Dually Branched Carbocyclic Nucleosides
Jin Woo Kim, Bo Gil Choi, Joon Hee Hong*
Antiviral agent, Branched carbocyclic nucleoside, Felkin-Anh model, [3,3]-Sigmatropic rearrangement
The stereoselective synthesis 4′,6′-dually branched carbocyclic nucleosides was accomplished in this study. The introduction of a methyl group in the 6′( α)-position was accomplished by Felkin-Anh controlled alkylation. The construction of the required 4′( α)-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.
1812 - 1816
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