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In the Hooker reaction (1936) an alkyl chain in a certain naphthoquinone (phenomenon first observed in the compound lapachol) is reduced by one methylene unit as carbon dioxide in each potassium permanganate oxidation.
Mechanistically oxidation causes ring-cleavage at the alkene group, extrusion of carbon dioxide in decarboxylation with subsequent ring-closure.
References
Hooker reaction Wikipedia(Text) CC BY-SA