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Synfacts 2009(1): 0056-0056  
DOI: 10.1055/s-0028-1087406
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Hydroacylation Applied to the Synthesis of Nucleoside Analogues

Contributor(s): Mark Lautens, Frédéric Ménard
P. Marcé, Y. Díaz, M. I. Matheu, S. Castillón*
Universitat Rovira i Virgili, Tarragona, Spain
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

A short and enantioselective synthesis of carbocyclic nucleosides is reported. The authors opted for a strategy involving an intra­molecular rhodium(I)-catalyzed asymmetric hydro-acylation step, which circumvents long reaction sequences previously reported to access carbo­cyclic intermediates 5 or 7. Both enantiomers of 6 are of interest for their potential antitumor and antiviral activity. Their synthesis is a powerful illustration of enantioselective hydroacylation.