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

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journal contribution
posted on 10.02.2000, 00:00 by Claudia W. Roberson, K. A. Woerpel
The formal synthesis of the alkaloid (±)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (±)-peduncularine.