Synthesis 2005(18): 3079-3084  
DOI: 10.1055/s-2005-918423
PAPER
© Georg Thieme Verlag Stuttgart · New York

Formal Enantioselective Synthesis of (-)-Carbovir and (-)-Abacavir: An Application of the Rhodium(I)-Catalysed Tandem Hydrosilylation-Intramolecular Aldol Reaction

Marta Freiría*a, Andrew J. Whiteheada, William B. Motherwellb
a Chemical Development Division, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK
Fax: +44(143)8764869; e-Mail: marta.x.freiria@gsk.com;
b Christopher Ingold Laboratories, Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UK
Further Information

Publication History

Received 1 June 2005
Publication Date:
12 October 2005 (online)

Abstract

An efficient synthesis of the highly potent anti-HIV carbocyclic nucleosides (-)-carbovir and (-)-abacavir has been accomplished from d-(-)-ribose using a rhodium(I)-catalysed tandem hydrosilylation-intramolecular aldol strategy to access a key intermediate.