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Issue 9, 2012
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Enantioselective synthesis of the carbocyclic nucleoside (−)-abacavir

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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

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Publication details

The article was received on 21 Oct 2011, accepted on 05 Dec 2011 and first published on 07 Dec 2011


Article type: Paper
DOI: 10.1039/C2OB06775G
Org. Biomol. Chem., 2012,10, 1870-1876

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    Enantioselective synthesis of the carbocyclic nucleoside (−)-abacavir

    G. A. Boyle, C. D. Edlin, Y. Li, D. C. Liotta, G. L. Morgans and C. C. Musonda, Org. Biomol. Chem., 2012, 10, 1870
    DOI: 10.1039/C2OB06775G

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