title: A concise route to dihydrobenzo[b]furans: formal total synthesis of (+)-lithospermic acid.
abstract: A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.
authors.affiliation: Eskitis Institute for Cell And Molecular Therapies, Griffith University, Nathan 4111 Queensland, Australia.
authors.forename: Joshua
authors.initials: J
authors.lastname: Fischer
authors.forename: G Paul
authors.initials: GP
authors.lastname: Savage
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Coster
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D001572:Benzofurans / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis; D002384:Catalysis; D053630:Depsides / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry
chemical_list: D019380:Anti-HIV Agents; D001572:Benzofurans; D001688:Biological Products; D053630:Depsides; C046833:lithospermic acid; D010165:Palladium