Issue 9, 2012
From the journal:

Organic & Biomolecular Chemistry

Enantioselective synthesis of the carbocyclic nucleoside (−)-abacavir†

Grant A. Boyle,a   Christopher D. Edlin,a   Yongfeng Li,b   Dennis C. Liotta,b   Garreth L. Morgans*a  and  Chitalu C. Musondaa  

* Corresponding authors

a iThemba Pharmaceuticals PTY (Ltd.), PO BOX 21, Modderfontein, Gauteng, South Africa
E-mail: gmorgans@ithembapharma.com
Fax: +27 (0)11 372-4518
Tel: +27 (0)11 372-4500

b Emory University, Department of Chemistry, 1521 Dickey Dr, Emerson 403, Atlanta, GA, USA
Tel: 404-727-8130

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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Article information

DOI
https://doi.org/10.1039/C2OB06775G
Article type
Paper
Submitted
21 Oct 2011
Accepted
05 Dec 2011
First published
07 Dec 2011

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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