KCS Publications

HOME > Search > Browsing(BKCS) > Archives

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

Title	Synthesis of Novel 4'α-Phenyl and 5'α-Methyl Branched Carbocyclic Nucleosides
Author	Chang Hyun Oh, Joon Hee Hong*
Keywords	Carbocyclic nucleoside, Antiviral agents, [3,3]-Sigmatropic rearrangement, Ring-closing metathesis
Abstract	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.
Page	1520 - 1524
Full Text	PDF

How to access to the WOL for The Bulletin of the Korean Chemical Society ?

The Bulletin of the Korean Chemical Society will be co-published with Wiley-VCH from 2015 towards. The online version of the Journal will thus be available on Wiley Online Library, Wiley(-VCH)'s global online platform.

KCS members can get a free online access to the Bulletin of the Korean Chemical Society in WOL.

Free Access to WOL