The total synthesis of (+/-)-tazettine (1) has been achieved in 16 steps from commercially available piperonyl alcohol in 11% overall yield. The crucial quaternary center was assembled by a novel [4+1] cycloaddition between dimethoxycarbene and beta-aryl vinyl isocyanate (4). Samarium diiodide conditions were employed to reduce the enamide unsaturation in the [2]benzopyrano[3,4-c]hydroindole intermediate 19 to compound 20 exhibiting a cis-AB ring fusion.