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@PHDTHESIS{Klischan:1037852,
      author       = {Klischan, Moritz},
      title        = {{B}iaryl-based natural products as structural motif for
                      pharmaceutically relevant compounds},
      volume       = {49},
      school       = {Düsseldorf},
      type         = {Dissertation},
      address      = {Jülich},
      publisher    = {Forschungszentrum Jülich GmbH Zentralbibliothek, Verlag},
      reportid     = {FZJ-2025-00995},
      isbn         = {978-3-95806-801-8},
      series       = {Bioorganische Chemie an der Heinrich-Heine-Universität im
                      Forschungszentrum Jülich},
      pages        = {V, 657},
      year         = {2025},
      note         = {Dissertation, Düsseldorf, 2024},
      abstract     = {Biaryls are important structural motifs for both
                      pharmaceutically relevant compounds as well as ligands, and
                      catalysts in chemical transformations. With the aim of
                      contributing to the everexpanding methodology towards
                      biaryls, different synthesis strategies were devised and
                      implemented to obtain synthetically relevant biaryls.
                      Moreover, stereoselective palladium catalyzed
                      transformations were investigated for the synthesis of
                      bicyclic compounds. 8,8′′-Biflavones, a class of
                      biaryl-based natural products, were investigated for their
                      bioactivity against various human pathogens. A synthesis
                      route for the construction of highly functionalized racemic
                      biaryl building blocks in three steps was established in a
                      scalable fashion. Enabled by this method, the first
                      extensive library of 8,8′′-biflavone analogues was
                      synthesized. This dedicated library was then evaluated
                      regarding its pharmaceutical potential in cooperation with
                      M.Sc. Lena Berning and M.Sc. Flaminia Mazzone (Heinrich
                      Heine University Düsseldorf). In addition to promising
                      results for these biflavones, bichalcones obtained as key
                      intermediates were identified as novel drug scaffolds. Based
                      on these first hits, further amino-8,8′′-biflavones
                      including the first non-C2-symmetrical 8,8′′-biflavone
                      were synthesized. In cooperation with M.Sc. Céline David
                      (Heinrich Heine University Düsseldorf) the structure
                      activity relationship was probed, and bioactivities
                      obtained. Next a strategy involving cyclic diaryliodonium
                      salts towards an enantiopure building block was implemented.
                      Extensive investigations were undertaken, and ultimately a
                      scalable protocol successfully established. These prochiral
                      building blocks were then applied to construct enantiopure
                      dimeric flavonoids and thus the usefulness of the
                      established methodology shown. In addition to these
                      investigations, palladium-catalyzed methods were
                      investigated to overcome advanced synthetic challenges. For
                      one, the Catellani reaction was used to obtain biaryls
                      inaccessible by state-of-the-art methods. Factors critical
                      for this transformation were identified, and a protocol for
                      the synthesis of tri-ortho-substituted biaryls established.
                      Moreover, first investigations into stereodynamic
                      biaryl-based palladacycles were conducted. The proposed
                      stereodynamics of these palladium complexes were supported
                      by preliminary computational calculations (DFT). Finally, in
                      collaboration with the working group of Prof. Mark Lautens
                      (University of Toronto), the use of chiral oxabicycles as
                      acetylene analogues was thoroughly investigated. A mechanism
                      to explain the observed stereoselectivity of the reaction
                      was proposed and supported by experimental findings.
                      Finally, DFT calculations were conducted to rationalize the
                      observed selectivities.},
      cin          = {IBOC},
      cid          = {I:(DE-Juel1)IBOC-20090406},
      pnm          = {2171 - Biological and environmental resources for
                      sustainable use (POF4-217) / GRK 2158 - Graduiertenkolleg
                      2158 – Naturstoffe und Analoga gegen Therapie-resistente
                      Tumoren und Mikroorganismen: Neue Leitstrukturen und
                      Wirkmechanismen (GRK-2158-20170406)},
      pid          = {G:(DE-HGF)POF4-2171 / G:(DE-Juel1)GRK-2158-20170406},
      typ          = {PUB:(DE-HGF)3 / PUB:(DE-HGF)11},
      url          = {https://juser.fz-juelich.de/record/1037852},
}