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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 10
BKCSDE 26(10)
October 20, 2005 

Synthesis of Novel 4'α-Phenyl and 5'α-Methyl Branched Carbocyclic Nucleosides
Chang Hyun Oh, Joon Hee Hong*
Carbocyclic nucleoside, Antiviral agents, [3,3]-Sigmatropic rearrangement, Ring-closing metathesis
This paper describes the racemic and stereoselective synthetic route for a novel 4'α-phenyl and 6'α-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'α-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.
1520 - 1524
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