Formal Synthesis of (±)-Peduncularine:  Use of the [3 + 2] Annulation of Allylic Silanes and Chlorosulfonyl Isocyanate

2000-02-10T00:00:00Z (GMT) by Claudia W. Roberson K. A. Woerpel
The formal synthesis of the alkaloid (±)-peduncularine (<b>1</b>) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane <b>6</b> with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam <b>7</b>. Conversion of this intermediate to <b>2</b> in three steps completed the formal synthesis of (±)-peduncularine.