title: Intermolecular radical cation Diels-Alder (RCDA) reaction of bicyclooctadienes: biomimetic formal total synthesis of kingianin A and total syntheses of kingianins D, F, H, and J.
abstract: Three endo bicyclooctadienol dimers corresponding to kingianins A and H, D, and F and J were obtained by the intermolecular radical cation Diels-Alder (RCDA) reaction. Each isomer was cleanly isolated without the aid of preparative HPLC. Kingianins D, F, H, and J were prepared by way of these intermediates from commercially available materials in 10, 13, 9, and 17 steps, respectively. Kingianin A has already been prepared from one of these compounds. Completion of the synthesis of kingianin H relied on Manchand's one-step, three-carbon homologation.
authors.affiliation: Department of Chemistry, Stony Brook University , Stony Brook, New York 11794, United States.
authors.forename: Hee Nam
authors.initials: HN
authors.lastname: Lim
authors.forename: Kathlyn A
authors.initials: KA
authors.lastname: Parker
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002412:Cations / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D002412:Cations; D011084:Polycyclic Aromatic Hydrocarbons; C553350:kingianin A