Accessing novel molecular scaffolds be they complex natural products with biological potential or bespoke molecular tools to probe biological function is dependent on the implementation of synthetic strategies that deliver material to enable biological evaluation. This talk will provide an overview of our research in St Andrews, where synthesis has played a central role in addressing biological questions and understanding role in human diseases. The first aspect will cover the discovery and development of a natural product inspired anti-trypanosomal agents from initial structural analogues to rationally designed small molecule inhibitors. Additionally, details of our research in the area of Gram-positve bacterial adhesion focused on the development of small molecule probes that intercept thioester domains within bacterial pilli.