Stereoselective Synthesis of 1′,2′-cis-Disubstituted Carbocyclic ribo-Nucleoside Analogues

Herein we disclose an efficient strategy for the convergent synthesis of 1′,2′-cis-disubstituted carbocyclic ribo-nucleoside analogues. Starting from an enantiomerically pure cyclopentenol precursor, the key step for the preparation of the highly functionalized carbocyclic building block is an asymmetric dihydroxylation. Employing different variants of the Mitsunobu protocol, the condensation with all-natural nucleobases or their precursors affords a series of ribo-configured carbocyclic 1′,2′-cis-disubstituted nucleoside analogues.