Synthesis of 3-indolyl-2,5-dihydroxybenzoquinones

Authors
Pirrung, MC Park, K Li, ZT
Citation
Mc. Pirrung et al., Synthesis of 3-indolyl-2,5-dihydroxybenzoquinones, ORG LETT, 3(3), 2001, pp. 365-367
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
3
Year of publication
2001
Pages
365 - 367
Database
ISI
SICI code
1523-7060(20010208)3:3<365:SO3>2.0.ZU;2-F
Abstract
[GRAPHICS] 3-indolylquinones can be efficiently prepared by the acid-catalyzed condens ation of indoles with 2,5- dichlorobenzoquinone, followed by DDQ oxidation, The resulting dichloroquinones are hydrolyzed to the 3-indolyldihydroxyben zoquinones. The 3-indolylquinone substructure is of interest because of its presence in natural products that modulate biological processes through pr otein-protein interactions, including the asterriquinones.