More than 50% of drugs currently on the market are either natural product inspired derivatives or natural products. Despite this remarkable feat, the pharmaceutical industry has partly abandoned this traditional method of drug discovery resulting in a decline of newly approved drugs. In this context, we propose the development of a novel Pd-catalyzed cascade reaction to gain highly efficient entry into the diketopiperazine framework. Using this newly developed chemical tool, analogs of natural products with confirmed quorum sensing or anticancer properties will be synthesized. Quorum sensing represents a novel therapeutic target to fight bacteria, which is especially attractive in light of the ever-expanding bacterial drug resistance, as it is based on bacterial cell-to-cell signaling disruption. Thus, we propose the synthesis of a series of diketopiperazine derivatives, based on the structure of known diketopiperazine based natural quorum sensing modulators. This task will additionally result in the implementation of a biological screening subunit within the host group. Furthermore, we aim to utilize the cascade reaction to access a series of tryprostatin A and B analogs (promising anticancer agents). A highly convergent approach is proposed herein, allowing for the synthesis of these chemical entities in half as many steps in comparison to the current “state-of-the-art” method. The synthesized derivatives will be assessed for their anticancer activity in collaboration with leading experts of the field. Thus, the proposed project entails a multidisciplinary, trans-national effort to find novel potent bioactive compounds that will certainly represent a high-quality contribution to advance the fields of Organic Chemistry, Medicinal Chemistry, Biology and Microbiology with a sustained positive impact on overall public health and welfare.