New divergent approaches to 2',3'-modified carbocyclic L-nucleoside analogues starting from enantiomerically pure (1R, 2S)- or (1S, 2R)-2-(benzyloxymethyl) cyclopent-3-enol are described. In the key step, stereochemically pure cyclopentanols were condensed with N3-protected thymine through a modified Mitsunobu protocol. Moreover, several routes to different cyclopentanol derivatives, to prepare carbocyclic L-2',3'-didehydro-2',3'-dideoxynucleosides (L-d4N), L-2',3' -dideoxynucleosides (L-ddN), and L-ribonucleosides are reported.