Totally twelve ((2-hydroxy-1-naphthyl))(3-(substituted phenyl)bicyclo [2.2.1]hept-5-ene-2-yl)methanones have been synthesized by fly-ash catalyzed water-mediated Diels-Alder [4+2] cycloaddition reaction. The synthesized bicyclic ketones were characterized by their physical constants, analytical and spectroscopic data. The antimicrobial and antioxidant activities of these bicyclic methanones were evaluated using Bauer-Kirby disc diffusion and diphenyl picrylhydrazyl(DPPH) radical scavenging technique. Most of the bicyclic methanones showed good antibacterial and antifungal activities against their microbial strains. The hydroxy- and methoxy- substituted methanones shows significant antioxidant activity.