Picrinine is a polycyclic akuammiline alkaloid isolated from the leaves of Alstonia scholaris nearly fifty years ago.  This presentation describes our efforts to complete the total synthesis of this complex natural product.  Featured in the synthesis is a palladium-catalyzed vinylation reaction to build the target's [3.3.1]-azabicyclic scaffold, in addition to a key Fischer indolization reaction to introduce the indoline functionality.  Our synthesis is the first known preparation of this long-standing synthetic challenge.

Total synthesis of the akuammiline alkaloid picrinine

248th National Meeting (2014)

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