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The Suzuki-Miyaura Cross-Coupling-Claisen Rearrangement-Cross-Metathesis Approach to Prenylated Isoflavones.
Kwesiga, George; Greese, Julia; Kelling, Alexandra; Sperlich, Eric; Schmidt, Bernd.
Afiliación
  • Kwesiga G; Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam, Germany.
  • Greese J; Department of Chemistry, Kabale University, P.O. Box 317, Kabale, Uganda.
  • Kelling A; Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam, Germany.
  • Sperlich E; Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam, Germany.
  • Schmidt B; Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam, Germany.
J Org Chem ; 88(3): 1649-1664, 2023 02 03.
Article en En | MEDLINE | ID: mdl-36633349
Isoflavones were synthesized via Suzuki-Miyaura coupling of 3-iodochromones and para-methoxybenzene- and para-phenolboronic acid. In our hands, conditions commonly used for similar cross couplings turned out to be unsuccessful or difficult to reproduce, for example, due to the unplanned partial cleavage of MOM-protecting groups. Using Pd(dba)2 as a precatalyst and tricyclohexylphosphine as an activating ligand, reliable cross-coupling conditions were identified. In all cases, notably higher yields of isoflavones were obtained with para-phenolboronic acid than with para-methoxybenzene boronic acid. This observation and the commercial availability of para-phenolboronic acid suggest that for the synthesis of the important 3'-prenyl- or 3',5'-diprenylisoflavone substitution pattern a synthetic route that introduces the prenyl substituents after the Pd-catalyzed cross-coupling step, thereby avoiding laborious and protecting-group-intensive multistep syntheses of C-prenylated arene boronic acids, is advantageous.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Isoflavonas Idioma: En Revista: J Org Chem Año: 2023 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Isoflavonas Idioma: En Revista: J Org Chem Año: 2023 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Estados Unidos