Enantioselective synthesis of the carbocyclic nucleoside (?)-abacavir?

Organic & Biomolecular Chemistry Pub Date: 2011-12-07 DOI: 10.1039/C2OB06775G

Abstract

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.

Graphical abstract: Enantioselective synthesis of the carbocyclic nucleoside (?)-abacavir
Recommended Literature