The photo Fries rearrangements of esters of 1-naphthol and 5-methoxy-l-naphthol to the corresponding l-hydroxy-2-acylnaphthalenes have been carried out. The best yield (70%) was obtained by irradiating 5methoxy-l-naphthyl acetate in ethyl acetate. By contrast the yield from 1-naphthyl acetate under similar conditions was 40%. Oxidation of l-hydroxy-5-methoxy-2-naphthyl cyclohexyl ketone with thallium trinitrate gave the corresponding 1,4-quinone. These results provide a method for the regioselective synthesis of tricyclic analogues of adriamycinone.

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Aus den beiden 1‐Naphtholen (I) werden nach bekannten Verfahren glatt die Ester (II)‐(IV) hergestellt und dann der Photo‐Fries‐Umlagerung unterworfen.