Oh, CH Hong, JH 2024-01-21T04:09:56Z 2024-01-21T04:09:56Z 2021-09-02 2005-10-20 0253-2964 https://pubs.kist.re.kr/handle/201004/136049 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 roup 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. English WILEY-V C H VERLAG GMBH S-ADENOSYLHOMOCYSTEINE HYDROLASE ANTI-HIV ACTIVITY METATHESIS 4&apos -AZIDOTHYMIDINE REARRANGEMENT NUCLEOTIDES MECHANISM ANALOGS Synthesis of novel 4 'alpha-phenyl and 5 'alpha-methyl branched carbocyclic nucleosides Article 1 BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.26, no.10, pp.1520 - 1524 BULLETIN OF THE KOREAN CHEMICAL SOCIETY 26 10 1520 1524 scie scopus kci ART000976417 000233211900012 2-s2.0-27844441841 Chemistry, Multidisciplinary Chemistry Article S-ADENOSYLHOMOCYSTEINE HYDROLASE ANTI-HIV ACTIVITY METATHESIS 4&apos -AZIDOTHYMIDINE REARRANGEMENT NUCLEOTIDES MECHANISM ANALOGS carbocyclic nucleoside antiviral agents [3,3]-sigmatropic rearrangement ring-closing metathesis