Synthesis of Bicyclo-DNA Nucleosides with Additional Functionalization in the Carbocyclic Ring

Author: Luisier Samuel   Leumann Christian J.  

Publisher: Swiss Chemical Society

ISSN: 0009-4293

Source: CHIMIA International Journal for Chemistry, Vol.62, Iss.4, 2008-04, pp. : 270-272

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Abstract

Two novel bicyclo nucleoside isomers carrying the base thymine in the furanose ring and an ester substituent in the carbocyclic ring were synthesized from a common bicyclic sugar precursor via a cyclopropanation/fragmentation pathway in nine steps. The relative configuration of the ester substituent in both isomers as well as the anomeric configuration in one nucleoside was determined by 1H-NMR difference NOE spectroscopy.