Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue

Bulletin of the Korean chemical society

Joon Hee Hong¹  Aihong Kim¹ 

关键词: Quaternary carbon;    Abacavir;    Claisen rearrangement;    Ring-closing metathesis;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

This paper discusses the racemic and stereoselective synthetic route for novel 4`�? -methyl and 6`�? -methyl analogues of abacavir. The quaternary carbon at the 4`-position of carbocyclic nucleoside was installed successfully via a Claisen rearrangement. The stereocontrolled construction of a methyl group in the 6`�? - position was directed through the Felkin-Anh rule. A Bis-vinyl compound 9 was cyclized successfully using Grubbs�? catalyst II to provide a carbocycle nucleus for the target compound. The synthesized compound 15 showed moderate anti-HIV activity (EC₅₀ = 10.67 �?M, MT-4 cell lines).

【 授权许可】

Unknown