Combination of the ring expansion of 3-t-butoxy-4-aryl-4-hydroxycyclobutenones to hydroxynaphthoquinones with the Hooker Oxidations of hydroxyquinones provides powerful methodolgy for the regiospecific synthesis of highly substituted naphthoquinones and related compounds. This combination is employed for the synthesis of the natural naphthoquinones, lomandrone and aristolindiquinone. © 1993.