title: Asymmetric total synthesis of (-)-panacene and correction of its relative configuration.
abstract: [reaction: see text] The first synthesis of (-)-panacene has been accomplished in concise, highly stereoselective fashion from commercially available 2-methoxy-6-methylbenzoic acid (15 steps, 8.3% overall yield). The synthesis unambiguously establishes the correct relative and absolute configuration of panacene, and demonstrates the serviceability of Pd(II)-mediated tandem intramolecular alkoxycarbonylation-lactonization for the expedient assembly of its tricyclic core, and the dual role of asymmetric alkynylation as an initial source of chirality and as a powerful tool for manipulating diastereoselectivity.
authors.affiliation: Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada. john.boukouvalas@chm.ulaval.ca
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas
authors.forename: Martin
authors.initials: M
authors.lastname: Pouliot
authors.forename: Joël
authors.initials: J
authors.lastname: Robichaud
authors.forename: Stephen
authors.initials: S
authors.lastname: MacNeil
authors.forename: Victor
authors.initials: V
authors.lastname: Snieckus
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D001048:Aplysia / Q000737:chemistry; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D006842:Hydrocarbons, Brominated; C519981:panacene; D010165:Palladium