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Synthesis of the aphin-related (±)-7,9-dideoxyquinone A and (±)-7,9-dideoxyquinone A'

Chorn, T.A., Giles, R.G.F., Green, I.R. and Mitchell, P.R.K. (1983) Synthesis of the aphin-related (±)-7,9-dideoxyquinone A and (±)-7,9-dideoxyquinone A'. Journal of the Chemical Society, Perkin Transactions 1 . pp. 1249-1254.

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The oxidative cyclisation of 3-(1-hydroxyethyl)-,1,4-dimethoxy-2-prop-1-enylnaphthalene with four equivalents of ceric ammonium nitrate to afford two 4-hydroxy-1,3-dimethylnaphtho[2,3-c]pyran-5,10-quinones with the same stereochemistry as quinones A and A′, derivatives of the aphid pigments protoaphin-fb and protoaphin-sl, is described. Certain aspects of the mechanism have been established.

Item Type: Journal Article
Publisher: Royal Society of Chemistry
Copyright: © 1983 Royal Society of Chemistry
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