Beticolins consist of a chlorinated tetrahydroxanthone linked to an anthraquinone subunit via a unique bicyclo[3.2.2]nonane ring system. A facile route towards naphthoquinone derivatives and subsequent Diels-Alder cycloadditions with functionalized dienes afforded a highly functionalized anthraquinone subunit of beticolin 0. For the installation of a tetrahydroxanthone subunit, a synthetic route was elaborated. With the obtained anthraquinone derivatives intramolecular couplings were performed under different conditions, to facilitate the construction of the bicyclo[3.2.2]nonane ring system. The formation of the desired scaffold turned out to be challenging, however a variety of novel bicyclo[3.3.1]systems was obtained, representing interesting scaffolds.
During a research stay at the University of Copenhagen, the functionalization of helical beta-peptoids was examined. Peptidomimetics adopting three-dimensional structures with well-defined display of functional groups while being resistant to proteolysis, are of interest for the development of foldamers with a desired function.
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