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Synfacts 2008(12): 1293-1293  
DOI: 10.1055/s-0028-1087327
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Application of an Enantioselective Cyclopentenone Synthesis

Contributor(s): Mark Lautens, Frédéric Ménard
A. Vázquez-Romero, J. Rodríguez, A. Lledó, X. Verdaguer*, A. Riera*
Universitat de Barcelona, Spain
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

Analogues of nucleosides are of interest for their antiviral and antitumor activity. Previous syntheses of carbanucleosides relied on enzymatic and kinetic resolution, or on sugar chirons. Using a highly enantioselective Pauson-Khand reaction, the tricyclic intermediate 3 was obtained in enantiopure form. Subsequent straightforward transformations led to precursor 4 without loss of ee, which could be converted in two steps into either abacavir or carbovir.