“…As exemplified by lysolipin I ( 1 , Figure ), elaborate xanthones present key structural features in a wide variety of complex natural products as well as a high number of bioactive agents. − Consequently, the development of efficient synthetic strategies toward these biologically important heterocycles presents an important research objective from the perspective of medicinal and synthetic chemistry. While a wide variety of different strategies to specific xanthones have been developed, these procedures still leave room for further improvement, in particular with respect to modularity and divergence. − As part of our studies to realize a first total synthesis of lysolipin I ( 1 ), a highly potent polycyclic antibiotic of bacterial origin, we became interested in the design of a flexible route to differently substituted halogenated xanthones. − In detail, elaborate xanthones bearing a bromide in either the 6- or the 7-position were required, to allow for a flexible coupling strategy to access the central phenanthrene core. Herein, we report the design, development, and application of a divergent coupling strategy to access different 6-bromo of the 7-bromoxanthones ( 3-6 ) starting from the same o -vanillin derivatives ( 7 , 8 ) and dibromoquinone 9 and the further elaboration of these xanthones by sequential Sonogashira couplings.…”