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Synthesis 2003(13): 2101-2109  
DOI: 10.1055/s-2003-41455
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

New Convergent Synthesis of Carbocyclic Nucleoside Analogues

Olaf R. Ludek, Chris Meier*
Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Fax: +49(40)428382495; e-Mail: chris.meier@chemie.uni-hamburg.de;
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Publikationsverlauf

Received 8 July 2003
Publikationsdatum:
10. September 2003 (online)

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Abstract

Two convergent approaches towards the synthesis of carbocyclic nucleoside analogs will be described. Both approaches start from the stereochemically pure cyclopentenol 8 that has been prepared enantioselectively from an alkylated cyclopentadiene. Using these approaches, carbocyclic analogues of dT, FdU and BVdU have been prepared. Moreover, the conversion into the cycloSal-pronucleotide and the corresponding nucleotide will be presented for one example.

Keywords

carbocyclic nucleosides - stereoselective synthesis - Mitsunobu reaction - cycloSal-pronucleotides - nucleotides

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Konrad M., Lavie A.; Mini-Rev. Med. Chem.; 2003, in press