Enantiomeric Synthesis of Novel Apiosyl Nucleosides as Potential Antiviral Agents
نویسندگان
چکیده
A series of 2',3'-dideoxy-3'-fluoro-D-apiosyl nucleosides 15, 16, 17 and 18 were synthesized enantiomerically with L-Gulonic-γ-lactone as the starting material. The reduction of butenolide 1 with DIBAL-H followed by the Luche procedure afforded the allylic alcohol 2. Ozonolysis and the reduction of compound 4 induced the cyclized lactol, which was acetylated to give the acetate 7. Condensation of the acetate 7 with silylated pyrimidine (N-benzoyl cytosine) and a purine base (6-chloropurine) under Vorbrüggen conditions and deblocking afforded a series of fluorinated apiosyl nucleosides.
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