Our synthetic efforts were focused on installing modifications that are commonly found in nature, e.g., halogenations, hydroxylation, and animation. Using 14 and 15 as a scaffold, halogenated and hydroxylated analogs were synthesized using one or two step reaction sequences (Schemes 1 and 2). First, the unoccupied 3-position of 14 was chlorinated by treatment with N-chlorosuccinimide and copper(II) chloride to yield chloro-menadione ( ) in decent yields (53%). Bromination of the same position involved treatment of 14 with bromine, sodium acetate, and acetic acid to yield bromomenadione (17) in moderate yields (71%). Similar halogenation reactions were also conducted on 15. Dichlorination of 15 was accomplished through treatment with thionyl chloride and pyridine to yield dichloro-naphthoquinone (18) in relatively poor yields (21%). Attempts to increase overall yields by converting 3 to 18 using similar reaction conditions led to 2-chloro-naphthoquinone (19), in good yields (77%). Dibromination of 15 was accomplished using the same conditions as the bromination of 14 but the reaction needed to be heated to produce 20 in decent yields (45%). Overall, the majority of the halogenation reactions proceeded very slowly and starting material was still observed when the reactions were quenched.