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

Marta Freiría; Andrew J. Whitehead; William B. Motherwell

doi:10.1055/s-2005-918423

PAPER

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

Marta Freiría*^a, Andrew J. Whitehead^a, William B. Motherwell^b
^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

Abstract

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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.

Key words

asymmetric synthesis - carbocyclic nucleosides - aldol reaction - hydrosilylation - rhodium

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