Collect. Czech. Chem. Commun. 2006, 71, 1011-1028

New and Efficient Synthesis of Racemic Cyclopent-3-en-1-yl Nucleoside Analogues and Their Derivatives

Bastian Reichardt, Olaf R. Ludek and Chris Meier*

Department of Chemistry, Institute of Organic Chemistry, Faculty of Mathematics, Informatics and Natural Sciences, University Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany


A new, efficient synthesis of racemic cyclopent-3-en-1-yl nucleoside analogues has been developed starting from cyclopentadiene. The key step is the regioselective hydroboration of an intermediately formed mixture of two alkylated cyclopentadienes to give one cyclopentenol. The remaining double bond was further functionalized by hydroboration, epoxidation, cis-hydroxylation and cyclopropanation.

Keywords: Nucleosides; Carbocyclic nucleosides; Cyclopentanes; Cyclopropanation; Hydroboration; Pyrimidines; Antivirals.

References: 26 live references.