Synthese enantiomerenreiner Tetrahydroxanthenone unter Verwendung Palladium-katalysierter Domino-Reaktionen (English shop)

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The tetrahydroxanthenone system constitutes the fundamental structural motif of various biologically active natural products which, with their antibacterial, cytostatic and antiviral properties, display an interesting activity profile.

This dissertation describes the development of a novel stereoselective approach to this class of compounds, whose key steps comprise the synthesis of chiral chromans by means of enantioselective domino Wacker–Heck and domino Wacker–carbonylation reactions. Oxidation of the chroman system to the chromanone and a subsequent intramolecular acylation afforded the tricyclic core skeleton.

Using the diastereoselective synthesis of 4-dehydroxydiversonol, the potential of this strategy for the synthesis of functionalised analogues was investigated.