Novel fluoro-substituted apio dideoxyuncleoside(($pm$)-3a and ($pm$)-3b) were efficiently synthesized stalling from 1,3-dihydroxyacetone via Horner-Emmons olefination as a key step. Cyclization of fluoro ester ($pm$)-6 under acidic conditions to the fluorolactone was smoothly proceeded in favor of trans-fluorolactone due to the favorable transition state with equatorial hydroxymethyl substituent. Unfortunately the final nucleosides($pm$) -3a and ($pm$)-3b were found to be inactive against several viruses such as HIV-1, HSV- I , HSV-2 and HCMV