title: Total synthesis of pareitropone via radical anion coupling.
abstract: A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.
authors.affiliation: Department of Chemical and Biological Engineering, Seoul National University, Seoul, 151-744, Republic of Korea.
authors.forename: Suk-Koo
authors.initials: SK
authors.lastname: Hong
authors.forename: Hyeonjeong
authors.initials: H
authors.lastname: Kim
authors.forename: Youngran
authors.initials: Y
authors.lastname: Seo
authors.forename: Sang Hyup
authors.initials: SH
authors.lastname: Lee
authors.forename: Jin Kun
authors.initials: JK
authors.lastname: Cha
authors.forename: Young Gyu
authors.initials: YG
authors.lastname: Kim
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000838:Anions; D001547:Benzaldehydes / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: C553778:2-bromoisovanillin; D000470:Alkaloids; D000838:Anions; D001547:Benzaldehydes; D006842:Hydrocarbons, Brominated; D007546:Isoquinolines; C467752:pareitropone