286931-55-3Relevant articles and documents
The synthesis of kermesic acid by acetylation-aided tautomerism of 6-chloro-2,5,8-trihydroxynaphtho-1,4-quinone
Bingham, Steve J.,Tyman, John H.P.
, p. 3471 - 3476 (2008/09/20)
Methodology has been sought towards obtaining a 2-chloro-1,4-naphthoquinone bearing hydroxyl groups in the adjoining ring for obtaining either kermesic or carminic acids. In the first of these objectives, kermesic acid has been synthesised from 6-chloro-2,5,8-trihydroxynaphtho-1,4-quinone by the regioselective cycloaddition of the 1,2-diacetate formed by its acetylation-aided tautomerism and cycloaddition with (E)- and (Z)-3-alkoxycarbonyl-2,4-bis(trimethylsilyloxy)penta-1,3-dienes. The parent unacetylated quinone resists cycloaddition.