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


  • Financial support from the National Science Foundation (CHE-1151563), the Department of Defense (NDSEG fellowship to S.M.K.), the Division of Organic Chemistry of the American Chemical Society (Graduate Research Fellowship to N.A.C., sponsored by Boehringer Ingelheim), the Searle Scholars Program, and Yale University is gratefully acknowledged. S.B.H. is a fellow of the Alfred P. Sloan and David and Lucile Packard Foundations, and is a Camille Dreyfus Teacher-Scholar.


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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.