Novel synthesis of 4'C-aryl-branched acyclic nucleoside using [3,3]-sigmatropic rearrangement
Gun Ha Baik1, Bong Young Chung, Chang-Hyun Oh
1Department of Chemistry, Korea University, Anam-dong, Sungbuk-ku, Seoul, South Korea.
Abstract:
A very efficient synthetic route for preparing a novel 4'-C-aryl branched-1',2'-seco-2',3'-dideoxy-2',3'-didehydro-nucleoside is described. Mesylate 7 was successfully synthesized via a Horner-Wadsworth-Emmons reaction and a [3,3]-sigmatropic rearrangement, with which an adenine base was coupled by nucleophilic substitution conditions (K2CO3, 18-Crown-6, DMF) to give the target nucleoside 9.
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