- The synthesis of kermesic acid by acetylation-aided tautomerism of 6-chloro-2,5,8-trihydroxynaphtho-1,4-quinone
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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.
- Bingham, Steve J.,Tyman, John H.P.
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p. 3471 - 3476
(2008/09/20)
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- The synthesis of kermesic acid by acetylation-aided tautomerism of 6- chloro-2,5,8-trihydroxynaphtho-1,4-quinone
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6-Chloro-2,5,8-trihydroxynaphtho-1,4-quinone does not undergo cycloaddition reactions but the 1,2-diacetate, 2-chloro-5,6-diacetoxy-8- hydroxynaphtho-1,4-quinone, formed by acetylation-aided tautomerism added (E)- and (Z)-3-alkoxycarbonyl-2,4-bis(trimethy
- Bingham, Steve J.,Tyman, John H. P.
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p. 925 - 926
(2007/10/03)
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