A novel strategy for the synthesis of high-density biofuel using two biomass-derived oxygenated compounds, furfural and guaiacol, with a variety of heterogeneous catalysts is proposed. In the first step of this strategy, furfural is converted with high yields and selectivity to cyclopentanol (CPOL) over Mg-Al supported Cu catalysts. Then, the cyclopentanol is used to alkylate guaiacol over a series of HY zeolites to generate C9–C16 oxygenates with an appropriate molecular weight to be used as transportation fuels. Finally, in the last step of this catalytic strategy, the C-alkylation products are successfully hydrodeoxygenated over ruthenium nanoparticles supported on carbon nanotubes (Ru/MWCNT), producing a liquid mixture of cyclic hydrocarbons with high density (0.865 g mL–1 at 20 °C) and excellent low-temperature properties. This overall reaction route is a promising approach for converting biomass-derived compounds into transportation fuel precursors.