An efficient stereoselective synthesis of furanoverrillin (<b>5</b>), a highly functionalized core of verrillin (<b>1</b>), is reported. The synthetic strategy is based on constructing bicyclic lactone <b>17</b> prior to the 10-membered ring macrocyclization. The effect of the C<sub>4</sub> methyl group on the furan reactivity is also discussed