title: Total synthesis and stereochemical revision of the chlorinated sesquiterpene (±)-gomerone c.
abstract: Revised: the total synthesis of gomerone C results in revision of the stereochemical assignment at C3. 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.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, Switzerland.
authors.forename: Nikolas
authors.initials: N
authors.lastname: Huwyler
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D006046:Gold / Q000737:chemistry; D054879:Halogenation; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; C581529:gomerone C; D006046:Gold