Synthesis of Polyalkoxymethylenedioxy-1,4-naphthoquinones from Parsley Seed Metabolite

A convenient synthesis of polyalkoxy-1,4-naphthoquinones, good starting materials for analogues of natural quinones, has been developed. Bromonaphthoquinone, more stable than its hydroxylated analogue, turned out to be a convenient and accessible key synthon for the preparation of various polyalkoxylated naphthoquinones. The obtained quinones could be useful starting materials for the preparation of biologically active polymethoxy- and hydroxy-methylenedioxynaphthoquinones.