title: Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions.
abstract: [reaction: see text] Two different routes to the tricyclic core of Garcinia-derived natural products are described. The first approach is based on a tandem Claisen/Diels-Alder rearrangement and delivers the desired lactone 14. The second approach, employing a Wessely oxidation/Diels-Alder protocol, leads to the same caged heterocycle, albeit with modified constitution.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
authors.forename: Eric J
authors.initials: EJ
authors.lastname: Tisdale
authors.forename: Chinmay
authors.initials: C
authors.lastname: Chowdhury
authors.forename: Binh G
authors.initials: BG
authors.lastname: Vong
authors.forename: Hongmei
authors.initials: H
authors.lastname: Li
authors.forename: Emmanuel A
authors.initials: EA
authors.lastname: Theodorakis
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D029760:Garcinia / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000179:Acrylates; D001688:Biological Products; C036658:acrylic acid