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Sandra M. King, Nicholas A. Calandra and Dr. Seth B. Herzon Total Syntheses of (−)-Acutumine and (−)-Dechloroacutumine Angewandte Chemie International Edition 52

Version of Record online: 20 FEB 2013 | DOI: 10.1002/anie.201210076

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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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