[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2005.26.10.1520

Synthesis of Novel 4'α-Phenyl and 5'α-Methyl Branched Carbocyclic Nucleosides

Oh, Chang-Hyun (Medicinal Chemistry Research Center, Korea Institute of Science and Technology)
Hong, Joon-Hee (College of Pharmacy, Chosun University)

Publication Information

Bulletin of the Korean Chemical Society / v.26, no.10, 2005 , pp. 1520-1524 More about this Journal

Abstract

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 group 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.

Keywords

Carbocyclic nucleoside; Antiviral agents; [3,3]-Sigmatropic rearrangement; Ring-closing metathesis;

Citations & Related Records

Times Cited By Web Of Science : 7 (Related Records In Web of Science)
Times Cited By SCOPUS : 1

Reference
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