title: Synthesis of 8-Phenylphenalenones: 2-Hydroxy-8-(4-hydroxyphenyl)-1H-phenalen-1-one from Eichhornia crassipes.
abstract: 2-Hydroxy-8-(4-hydroxyphenyl)-1H-phenalen-1-one (1), the first reported 8-phenylphenalenone from the roots of Eichhornia crassipes (water hyacinth), was synthesized starting from 2-methoxynaphthalene in 11 steps and with an overall yield of 2%. A cascade Friedel-Crafts/Michael annulation reaction between acryloyl chloride and 2-methoxynaphthalene afforded 9-methoxyperinaphthanone that, after transformation to 9-methoxy-2-(4-methoxyphenyl)-1H-phenalen-1-one by means of standard Suzuki-Miyaura methodology, was subjected to a reductive carbonyl transposition to afford 8-(4-methoxyphenyl)perinaphthanone. Dehydrogenation, epoxidation, and demethylation of the latter afforded 1.
authors.affiliation: Instituto de Química, Síntesis y Biosíntesis de Metabolitos Naturales, Universidad de Antioquia , AA 1226 Medellín, Colombia.
authors.forename: Felipe
authors.initials: F
authors.lastname: Ospina
authors.affiliation: Max Planck Institute für Chemische Ökologie , Beutenberg Campus, Hans-Knöll-Strasse 8, 07745 Jena, Germany.
authors.forename: William
authors.initials: W
authors.lastname: Hidalgo
authors.affiliation: Instituto de Química, Síntesis y Biosíntesis de Metabolitos Naturales, Universidad de Antioquia , AA 1226 Medellín, Colombia.
authors.forename: Marisol
authors.initials: M
authors.lastname: Cano
authors.affiliation: Max Planck Institute für Chemische Ökologie , Beutenberg Campus, Hans-Knöll-Strasse 8, 07745 Jena, Germany.
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
authors.affiliation: Instituto de Química, Síntesis y Biosíntesis de Metabolitos Naturales, Universidad de Antioquia , AA 1226 Medellín, Colombia.
authors.forename: Felipe
authors.initials: F
authors.lastname: Otálvaro