Diversity-oriented synthesis is a synthetic methodology aimed at the generation of diverse collections of molecules, often structurally complex and representative of large regions of chemical space, typically from simple starting materials. This approach investigates strategies that prioritize the creation of molecular scaffolds and structural diversity over linear analogue synthesis, employing techniques such as multi-component reactions, cyclizations, and other scaffold-generating transformations. The field is significant for accessing novel chemical space and privileged structures, which are valuable for applications in chemical biology and drug discovery.