The asymmetric synthesis route and the racemic route above are short and efficient ways to diverse carbocyclic D
- or L
-nucleosides (Scheme 2). Different heterocycles can be condensed to these precursors leading to carbocyclic purine- and pyrimidine-nucleosides. Beside α- and β-nucleosides, carbocyclic epi- and iso-nucleosides in the 2’-deoxyxylose form were accessable.
What else is possible?
The racemic cyclopentenol 6
can be coupled by a modified Mitsunobu-reaction. Moreover, this strategy offers the possibility of synthesizing new carbocyclic nucleosides by functionalizing the double bond before or after introduction of the nucleobase (scheme 3).
Scheme 3: Functionalized carbocyclic nucleosides based on cyclopentenol 6
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