title: Synthesis of (-)-oxycodone.
abstract: Our novel synthetic route to (-)-oxycodone, a semisynthetic opioid analgesic, features a palladium-catalyzed direct intramolecular arylation of an aryl bromide, oxidative dearomatization of a dihydrophenanthrenol, formation of a benzylic quaternary carbon by an intramolecular Michael addition of a malonate moiety, and construction of the morphinan skeleton via a Hofmann rearrangement/lactamization cascade.
authors.affiliation: †Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kimishima
authors.affiliation: †Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.|‡Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
authors.forename: Hirotatsu
authors.initials: H
authors.lastname: Umihara
authors.affiliation: †Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Mizoguchi
authors.affiliation: ‡Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yokoshima
authors.affiliation: ‡Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D015394:Molecular Structure; D010098:Oxycodone / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000701:Analgesics, Opioid; D006842:Hydrocarbons, Brominated; D010165:Palladium; D010098:Oxycodone