• Bulletin of the Korean Chemical Society
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• v.32 no.2
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• pp.411-416
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• 2011

Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-group with antiviral enhancement, novel 4'-hydroxymethyl-5'-norcarbocyclic adenosine phosphonic acid analogues were designed and synthesized from 2,2-dimethyl-1,3-dioxolane-4-ethanol (5) using reiterative Grignard addition and ring-closing metathesis (RCM) as key reactions. The synthesized adenosine phosphonic acids analogues (22) and (23) were subjected to antiviral screening against HIV-1. Compound (23) exhibited moderate anti-HIV activity ($EC_50$ = 8.61 ${\mu}M$) in the CEM cell line.

• Archives of Pharmacal Research
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• v.28 no.10
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• pp.1105-1110
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• 2005

Novel anomeric branched carbocyclic nucleosides were synthesized from 1,3-dihydroxy acetone. 4'-Hydroxymethyl was installed by [3,3]-sigmatropic rearrangement reaction and 1'-methyl group was introduced by carbonyl addition of methylmagnesium bromide. The coupling of nucleosidic bases and desilylation afforded a series of novel nucleosides. The synthesized compounds $16{\~}19$ were evaluated for their antiviral activity against HIV-1, HSV-1, HSV-2, and EMCV. Compounds 16 and 19 exhibit toxicity non-related to any anti-HIV-1 activity.

• Bulletin of the Korean Chemical Society
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• v.25 no.12
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• pp.1812-1816
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• 2004

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.