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.
Pirrung
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MC
Department of Chemistry, Levine Science Research Center, Duke University, Box 90317, Durham, North Carolina 27708, USA. pirrung@chem.duke.edu
Park
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K
Li
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D016227:Benzoquinones / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*
D016227:Benzoquinones; D007211:Indoles