title: Total synthesis of the antitumor antibiotic (+/-)-fredericamycin A by a linear approach.
abstract: A linear approach to the total synthesis of racemic fredericamycin A (1) through the oxidative intramolecular [4 + 2] cycloaddition of a (phenylthio)acetylene-cobalt complex is described, which is applicable for the asymmetric total synthesis of naturally occuring 1. The highlight of this work is the aromatic Pummerer-type reaction with 1-ethoxyvinyl chloroacetate, which effects the introduction of the oxygen functional group to the internal B-ring of the highly functionalized, congested polyaromatic ABC-ring moiety.
authors: Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Japan. kita@phs.osaka-u.ac.jp
authors: Y
authors: Y
authors: Kita
authors: K
authors: K
authors: Iio
authors: K
authors: K
authors: Kawaguchi
authors: N
authors: N
authors: Fukuda
authors: Y
authors: Y
authors: Takeda
authors: H
authors: H
authors: Ueno
authors: R
authors: R
authors: Okunaka
authors: K
authors: K
authors: Higuchi
authors: T
authors: T
authors: Tsujino
authors: H
authors: H
authors: Fujioka
authors: S
authors: S
authors: Akai
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D003500:Cyclization; D007546:Isoquinolines / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000903:Antibiotics, Antineoplastic; D007546:Isoquinolines; D013141:Spiro Compounds; C016660:fredericamycin A