Enantioselective synthesis of the carbocyclic nucleoside (−)-abacavir

作者：Grant A. Boyle, Christopher D. Edlin, Yongfeng Li, Dennis C. Liotta, Garreth L. Morgans, Chitalu C. Musonda · 发表于：Organic & Biomolecular Chemistry · 年份：2011 · DOI：10.1039/c2ob06775g · 被引用次数：23 · 研究领域：HIV Research and Treatment、HIV/AIDS drug development and treatment、Carbohydrate Chemistry and Synthesis

An enantiopure β-lactam with a suitably disposed electron withdrawing group on nitrogen, participated in a π-allylpalladium mediated reaction with 2,6-dichloropurine tetrabutylammonium salt to afford an advanced cis-1,4-substituted cyclopentenoid with both high regio- and stereoselectivity. This advanced intermediate was successfully manipulated to the total synthesis of (-)-Abacavir.