title: The [5+5] route to the phenanthrene skeleton.
abstract: This account describes the historical development of the coupling of γ,δ-unsaturated Fischer carbene complexes ando-alkynylbenzaldehydes, which directly affords hydrophenanthrene ring systems in a process where each reactant contributes five carbons to the newly-formed bicyclo[4.4.0]decane ring system. The process has been termed net [5+5] cycloaddition. Use of the reaction to produce various medicinally important natural products and/or their parent ring systems is discussed.
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico, 88003, USA.
authors.forename: James W
authors.initials: JW
authors.lastname: Herndon
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico, 88003, USA.
authors.forename: Bishnu
authors.initials: B
authors.lastname: Dhakal
keywords: Diels-Alder reactions; Fischer carbene complexes; alkynes; annulation; cycloaddition; isobenzofurans; phenanthrenes