Synthesis of 3-Indolyl-2,5-dihydroxybenzoquinones

Synthesis of 3-Indolyl-2,5-dihydroxybenzoquinones

3-Indolylquinones can be efficiently prepared by the acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone, followed by DDQ oxidation. The resulting dichloroquinones are hydrolyzed to the 3-indolyldihydroxybenzoquinones. The 3-indolylquinone substructure is of interest because of its...

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Veröffentlicht in:Organic letters 2001-02, Vol.3 (3), p.365-367
Hauptverfasser: Pirrung, Michael C, Park, Kaapjoo, Li, Zhitao
Format: Artikel
Sprache:eng
Schlagworte:
Benzoquinones - chemical synthesis
Indoles - chemical synthesis
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Zusammenfassung:3-Indolylquinones can be efficiently prepared by the acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone, followed by DDQ oxidation. The resulting dichloroquinones are hydrolyzed to the 3-indolyldihydroxybenzoquinones. 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006852l