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Nikolas Huwyler and Prof. Dr. Erick M. Carreira Total Synthesis and Stereochemical Revision of the Chlorinated Sesquiterpene (±)-Gomerone C Angewandte Chemie International Edition 51

Article first published online: 14 NOV 2012 | DOI: 10.1002/anie.201207203

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Revised: The total synthesis of gomerone C results in revision of the stereochemical assignment at C3 (see scheme). The synthetic strategy relies on a late-stage Conia-ene reaction, which efficiently forms the bicyclo[3.2.1]octane containing the bridgehead chloride and generates an exocyclic olefin, which can be used as a flexible handle for further elaboration. The two contiguous quaternary centers are installed by means of a Diels–Alder reaction.

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