Total synthesis of (±)-tazettine

JH Rigby, A Cavezza, MJ Heeg

Index: Rigby, James H.; Cavezza, Alexandre; Heeg, Mary Jane Journal of the American Chemical Society, 1998 , vol. 120, # 15 p. 3664 - 3670

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Citation Number: 72

Abstract

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 ...