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Application of Cyclic Diaryliodonium Salts in the Synthesis of Axially Chiral Natural Product Analogues.
Klischan, Moritz K T; David, Céline; Grudzinski, Daniel; Frey, Wolfgang; Stork, Björn; Pietruszka, Jörg.
Affiliation
  • Klischan MKT; Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Mathematisch-Naturwissenschaftliche Fakultät, Institut für Bioorganische Chemie, 52428 Jülich, Germany.
  • David C; Institute of Molecular Medicine I, Medical Faculty and University Hospital Düsseldorf, Heinrich Heine University Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany.
  • Grudzinski D; Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Mathematisch-Naturwissenschaftliche Fakultät, Institut für Bioorganische Chemie, 52428 Jülich, Germany.
  • Frey W; Institute of Organic Chemistry, University of Stuttgart, 70569 Stuttgart, Germany.
  • Stork B; Institute of Molecular Medicine I, Medical Faculty and University Hospital Düsseldorf, Heinrich Heine University Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany.
  • Pietruszka J; Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Mathematisch-Naturwissenschaftliche Fakultät, Institut für Bioorganische Chemie, 52428 Jülich, Germany.
Org Lett ; 26(25): 5258-5262, 2024 Jun 28.
Article in En | MEDLINE | ID: mdl-38885455
ABSTRACT
The application of cyclic diaryliodonium salts in the synthesis of bioactive natural product analogues was demonstrated. Axially chiral biaryls were obtained via the enantioselective ring opening of cyclic diaryliodonium salts. Regioselective borylation was key in accessing both enantiomers of a biphenol key intermediate in eight steps overall. 8,8″-Amino biflavones were synthesized, their bioactivity profiled, and the eutomer identified. The structure-activity relationship was probed.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2024 Document type: Article Affiliation country: Germany
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2024 Document type: Article Affiliation country: Germany