Abstract :
The article highlights how an analysis of the natural product arboridinine pinpointed two key elements of structural similarity which suggests the value of a metal-mediated 6-endo-dig cyclization to fashion its tetracyclic indolenine core. The power of the latter design element is highlighted by several failures in achieving similar functional group patterning through more traditional aza-Prins and Mannich cyclization strategies. The operations fuel an inaugural 13-step racemic synthesis of the target.