Synthesis of 3-indolyl-2,5-dihydroxybenzoquinones

[figure: see text] 3-Indolylquinones can be efficiently prepared by the acid-catalyzed condensation of Indoles with 2,5-dichiorobenzoquinone, followed by DDQ oxidation. The resulting dichloroquinones are hydrolyzed to the 3-indolyidihydroxybenzoquinones. The 3-indolylquinone substructure is of interest because of its presence in natural products that modulate biological processes through protein-protein interactions, including the asterriquinones.