Total Syntheses of (−)-Acutumine and (−)-Dechloroacutumine

One route fits all: Syntheses of the title complex tetracyclic alkaloids are described. The routes feature the strategic application of 5‐trimethylsilylcyclopentadiene, a selective hydrostannylation of a complex enyne, a Hosomi–Sakurai cyclization to form the skeleton of the targets, an allylic formate rearrangement to construct the spirocyclopentenone rings, and a selective hydrogenation to establish the alkyl chloride functional group of (−)‐acutumine.