Abstract
Several synthetic routes to mono- and dihydroxynaphthazarins bearing an acetyl side-chain have been explored. Methoxynaphthazarin 1 has always been the starting material. Acylation is brought about via a photo-Fries rearrangement of various adequately substituted acetoxynaphthalenes prepared in several steps from 1. Further steps including oxidative demethylation, hydrolysis and ether cleavage reactions, led to the desired mono- and dihydroxysubstituted acetylnaphthazarins. A new synthesis of Spinochrome A 24, a natural occurring pigment representative of this kind of naphthazarin derivatives, is described.
Published Version
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