Total Synthesis of (±)-Nominine, a Heptacyclic Hetisine-Type Aconite Alkaloid


  • We thank Professor Emeritus Shin-ichiro Sakai and Professor Hiromitsu Takayama of Chiba University for providing a sample of natural nominine.


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The barrier has finally been lifted to the synthesis of hetisine-type alkaloids with the total synthesis of (±)-nominine (1) in 40 steps from 2-bromo-5-methoxyphenethyl iodide. Key steps in the construction of the architecturally complex polycyclic structure of this natural product were a radical cyclization of an enyne and a palladium-catalyzed intramolecular α arylation of an aldehyde.