Synthesis of a Focused Chemical Library Based on Derivatives of Embelin, a Natural Product with Proapoptotic and Anticancer Properties

The synthesis of new derivatives of embelin, a natural inhibitor of X-linked inhibitor of apoptosis protein (XIAP) is described. The design of these new molecules involved introduction of aromatic groups directly linked to the benzoquinone core. To allow a large flexibility in the nature and the length of the added chain, the strategy involves first a Suzuki-Miyaura reaction with functionalized aromatics, yielding a first generation of molecules. Then, by appropriate use of the functional groups, a second generation of representative embelin derivatives was prepared.