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.
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