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Paper | Regular issue | Vol 48, No. 3, 1998, pp.491-498
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8068
Syntheses of Novel Acyclic Nucleosides, 9-(4'-Hydroxy-2'-methylbut-1'-enyl)-adenine and Related Compounds

Changmei Cheng, Tetsuro Shimo, Kenichi Somekawa,* and Masanori Baba

*Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Kagoshima University, Korimoto, Kagoshima 890, Japan


An exploratory coupling reaction between adenine and a protected vicinal dibromo-intermediate was carried out to give the β,γ-unsaturated nucleoside analogues and a vinyl bromide derivative. Then a novel CuI catalytic coupling reaction between adenine and the vinyl bromide was successfully developed to afford an α,β-unsaturated acyclic nucleoside, 9-(4’-hydroxy-2’-methylbut-1’-enyl)adenine. All the above nucleosides were subjected to an anti-HIV-1 test.