Lignans and related phenols. Part 18. The synthesis of quinones from podophyllotoxin and its analogues

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Abstract
The preparation of quinones from podophyllotoxin and peltatins of the aryltetrahydronaphthalene class by oxidative demethylation is described. The derivation of 2′-substituted ortho-quinones from these products by the reductive addition of azide, bromide, and chloride and subsequent oxidation by periodate is reported. Acid-catalysed reactions of ortho-quinones with alcohols are described including an unusual example of reductive methylation.

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