Gabosines constitute a group of naturally occurring compounds with unique structures that exhibit very interesting biological activities. Synthetic efforts have been continuously reported since 1985. In this work, multistep total syntheses of natural gabosine H and non-natural gabosines have been accomplished by using a chemoenzymatic approach. Chirality was transferred from the starting material 3-methyl-<i>cis</i>-1,2-cyclohexadienediol, which was obtained by biotransformation of toluene. Protection of the diol followed by iodohydroxylation or dihydroxylation of the less hindered double bond and further functional group transformations, permitted us to build up the synthetic sequences to the final products. The chemical structures and the absolute configurations of two key intermediates and two final products were confirmed by X-ray diffraction.