title: Enantioselective total synthesis of (S)-bisoranjidiol, an axially chiral bisanthraquinone.
abstract: The first enantioselective total synthesis of the bisanthraquinone (S)-bisoranjidiol and an unnatural regioisomer has been accomplished. Key features of the synthesis include the asymmetric oxidative biaryl coupling of a hindered 8-substituted 2-naphthol, selective para-quinone formation, and regioselective tandem Diels-Alder/aromatization reactions.
authors.affiliation: Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
authors.forename: Erin E
authors.initials: EE
authors.lastname: Podlesny
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009284:Naphthols; D019666:Rubiaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C572380:(S)-bisoranjidiol; D000880:Anthraquinones; D009284:Naphthols; C028405:2-naphthol