Novel synthesis of 4'C-aryl-branched acyclic nucleoside using [3,3]-sigmatropic rearrangement.
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.
Baik
Gun Ha
GH
Department of Chemistry, Korea University, Anam-dong, Sungbuk-ku, Seoul, South Korea.
Chung
Bong Young
BY
Oh
Chang-Hyun
CH
Cho
Jung-Hyuck
JH
Ko
Ok Hyun
OH
Hong
Joon Hee
JH
D000225:Adenine / Q000737:chemistry; D019380:Anti-HIV Agents / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*
D019380:Anti-HIV Agents; D009705:Nucleosides; D000225:Adenine