Readily available C-acylated cycloalkanones undergo efficient Cu and Pd-catalyzed ring closure providing a range of tetrahydroxanthones and related structures. This contribution will describe the optimization of this chemistry and its application to a range of substrates. Using tandem catalysis, this chemistry can be combined with Suzuki cross-couplings to provide 7-arylated tetrahydroxanthones in a single operation. In further work, we show that one of the synthesized derivatives selectively kills pancreatic cancer (PANC-1) cells under conditions of nutrient deprivation indicating that the tetrahydroxanthone nucleus is responsible at least in part for the �anti-austerity� effects of the naturally occurring kigamicins.

Biologically active tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond construction

242nd National Meeting (2011)

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