title: Enantioselective synthesis of the carbocyclic nucleoside (-)-abacavir.
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.
authors.affiliation: iThemba Pharmaceuticals PTY (Ltd.), Gauteng, South Africa.
authors.forename: Grant A
authors.initials: GA
authors.lastname: Boyle
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Edlin
authors.forename: Yongfeng
authors.initials: Y
authors.lastname: Li
authors.forename: Dennis C
authors.initials: DC
authors.lastname: Liotta
authors.forename: Garreth L
authors.initials: GL
authors.lastname: Morgans
authors.forename: Chitalu C
authors.initials: CC
authors.lastname: Musonda
mesh_terms: D000818:Animals; D002802:Cholinesterases / Q000378:metabolism; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D008049:Lipase / Q000378:metabolism; D015394:Molecular Structure; D011551:Pseudomonas fluorescens / Q000201:enzymology; D013237:Stereoisomerism; D013552:Swine; D000099227:Abacavir
chemical_list: D002802:Cholinesterases; D015224:Dideoxynucleosides; D008049:Lipase; D000099227:Abacavir