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 β-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 ...
