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.
T. A. Chorn, R. G. F. Giles, I. R. Green and P. R. K. Mitchell, J. Chem. Soc., Perkin Trans. 1, 1983, 1249 DOI: 10.1039/P19830001249
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