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. 2012 Mar 7;10(9):1870-6.
doi: 10.1039/c2ob06775g. Epub 2012 Jan 25.

Enantioselective synthesis of the carbocyclic nucleoside (-)-abacavir

Grant A Boyle  1 , Christopher D Edlin, Yongfeng Li, Dennis C Liotta, Garreth L Morgans, Chitalu C Musonda
Affiliations

Enantioselective synthesis of the carbocyclic nucleoside (-)-abacavir

Grant A Boyle et al. Org Biomol Chem. .

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.

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