• YAKHAK HOEJI
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• v.47 no.6
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• pp.417-421
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• 2003

This paper describes a synthetic route to novel 2'-methyl and 4'-hydroxy carbocyclic nucleosides. The methyl group was successfully installed by carbonyl addition reaction of isopropenyl magnesium bromide followed by ring-closing metathesis and the hydroxy group was directly introduced from carbohydrate chiral template "D-lactose".ose".uot;.

• Archives of Pharmacal Research
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• v.29 no.6
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• pp.464-468
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• 2006

Novel phenyl branched apiosyl nucleosides were synthesized in this study. The introduction of phenyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement. Apiosyl sugar moiety was constructed by sequential ozonolysis and reductions. The natural bases (cytosine and adenine) were efficiently coupled with an apiosyl sugar by classical glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2 and HCMV.

• YAKHAK HOEJI
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• v.48 no.1
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• pp.88-92
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• 2004

In this study; a series of 2',4'-doubly branched carbocyclic nucleosides (8,9,10) were synthesized from simple acyclic ketone derivative as starting material. The installation of the 4'-quaternary carbon needed was carried out using a 〔3,3〕-sigmatropic rearrangement. In addition, the introduction of a methyl group in the 2'-position was accomplished by Grig-nard reaction. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst. Although all the synthesized compounds were assayed against several viruses, only cytosine analogue 9 showed weak antiviral viral activity (EC$_{50}$=45.4 $\mu$M) against CoxB3 virus.s.

• YAKHAK HOEJI
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• v.49 no.1
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• pp.20-24
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• 2005

The synthesis of 4',5'-doubly branched carbocyclic nucleosides was accomplished in this study. The selective methylation in the 5'-position was made by Felkin-Anh controlled Grignard addition. The construction of the required 4'-quaternary carbon was carried out by using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural pyrimidine bases (cytosine, uracil, thymine) 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 weak antiviral activity against the HCMV.

• 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.

• Bulletin of the Korean Chemical Society
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• v.31 no.11
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• pp.3348-3352
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• 2010

Novel 4'-ethyl-5'-norcarbocyclic adenosine phosphonic acid analogues were synthesized from propionaldehyde 5 through a de novo acyclic synthetic route using reiterative Grignard additions and ring-closing metathesis (RCM) as key reactions. The synthesized nucleoside phosphonic acids analogues 17, 18, 19, and 21 were subjected to antiviral screening against human immunodeficiency virus.

• Bulletin of the Korean Chemical Society
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• v.35 no.9
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• pp.2743-2748
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• 2014

Novel 4'-trifluoromethyl-5'-norcarbocyclic purine phosphonic acid analogs were efficiently synthesized from commercially available 1,3-dihydroxy cyclopentane (5). Trifluoromethylation was successfully performed by using the Ruppert-Prakash reaction. The purine nucleosidic bases were efficiently coupled by using the Mitsunobu reaction. The synthesized adenosine phosphonic acids analogs 13 and 16 were screened for antiviral activity against human immunodeficiency virus-1 (HIV-1). Adenine derivative 13 exhibited significant anti-HIV-1 activity.