Total synthesis of perylene quinone mycotoxins

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Infestation of food and feed with mould fungi leads to crop losses and due the fungal toxins (mycotoxins) to severe health problems. Alternaria metabolites are a less investigated class of toxins; especially important are the resorcylic lactones and the perylene quinones. Though some of the perylene quinone toxins are highly toxic, hardly any of these were thoroughly investigated, not all of their structures are not unambiguously clear, and no total synthesis is available, which could supply sufficient amounts of the toxins for biological investigations. In this proposal we describe total syntheses, which would lead to several perylene quinone toxins. Toxins with a biphenyl substructure should be accessible from either naphthalene-1,5-diol or from biphenyl-alpha,alpha'-dicarbaldehyde and toxins with a dihydroanthracene substructure could be approached starting with tetralin-1,5-diol. Key reactions would be inter alia olefinations, electrophilic aromatic acylations, and Meinwald rearrangements. Further transformation would be epoxidations, opening of epoxides, dihydroxylations, and alpha,beta-dehydrations of carbonyl compounds, depending on the respective target toxin.