Enantioselective synthesis of the carbocyclic nucleoside ()-abacavirElectronic supplementary information (ESI) available: Copies of 1H NMR and 13C NMR spectra of new compounds. See DOI: 10.1039/c2ob06775g

An enantiopure -lactam with a suitably disposed electron withdrawing group on nitrogen, participated in a -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 adva...

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Bibliographic Details
Main Authors Boyle, Grant A, Edlin, Christopher D, Li, Yongfeng, Liotta, Dennis C, Morgans, Garreth L, Musonda, Chitalu C
Format Journal Article
LanguageEnglish
Published 09.02.2012
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Summary:An enantiopure -lactam with a suitably disposed electron withdrawing group on nitrogen, participated in a -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. A route to the carbocyclic nucleoside ()-Abacavir starting from a readily available -lactam is described.
Bibliography:1
H NMR and
13
C NMR spectra of new compounds. See DOI
Electronic supplementary information (ESI) available: Copies of
10.1039/c2ob06775g
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob06775g