Enantiomeric Synthesis of Novel Apiosyl Nucleosides as Potential Antiviral Agents

Bulletin of the Korean chemical society

Joon Hee Hong¹  Aihong Kim¹ 

关键词: Apiosyl nucleosides;    Claisen rearrangement;    Luche procedure;    Antiviral agents;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

A series of 2`,3`-dideoxy-3`-fluoro-D-apiosyl nucleosides 15, 16, 17 and 18 were synthesized enantiomerically with L-Gulonic- �?-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 (N4-benzoyl cytosine) and a purine base (6-chloropurine) under Vorbruggen conditions and deblocking afforded a series of fluorinated apiosyl nucleosides.

【 授权许可】

Unknown