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M. Sc. Darius D. Schwarzer, Dipl.-Ing. Philipp J. Gritsch and Dr. Tanja Gaich Mimicking Dimethylallyltryptophan Synthase: Experimental Evidence for a Biosynthetic Cope Rearrangement Process Angewandte Chemie International Edition 51

Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201203586

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Easy to cope with: Experimental evidence was found to support an enzymatic [3,3]-sigmatropic rearrangement catalyzed by dimethylallyltryptophan (DMAT) synthase (see scheme). A bio-inspired system showed the feasibility of Cope rearrangement to the C-4 position of the indole nucleus. The tricyclic benzo[cd]indole core of welwitindolinones and dragmacidin E was synthesized using this transformation.

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