Abstract: Various approaches to the synthesis of menaquinones have been studied in which the aromatic component is activated to encourage nucleophilic attack upon a receptive prenyl fragment. Thus alkylation of the potassium salt of 2-methyl-1, 4-naphthoquinol or 4- methoxy-3-methyl-1-naphthol with geranyl bromide gave menaquinone-2 in 20 and 45% yield, re-spectively, following oxidation to the quinone. Hydrogenolysis of the dimethyl ...