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For decades, akuammiline alkaloids have attracted synthetic chemists due to their intriguing molecular architecture. Among the different structural elements embedded in their carboskeleton, the methanoquinolizidine system constitutes the signature structural element of this alkaloid family. Herein, we describe a novel synthetic access to this system which relies on a [2,3]-Stevens rearrangement and results in the formal synthesis of strictamine.

Formal total synthesis of (±)-strictamine – the [2,3]-Stevens rearrangement for construction of octahydro-2H-2,8-methanoquinolizines