Total Synthesis and Stereochemical Revision of the Chlorinated Sesquiterpene (±)-Gomerone C


  • We are grateful to Dr. B. Schweizer and M. Solar for X-ray crystallographic analysis, and to Dr. M.-O. Ebert, R. Arnold, R. Frankenstein, and P. Zumbrunnen for NMR measurements.


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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.