Matrix meetalloproteinases (MMPs) are a therapeutic target for many pharmaceutical companies as they are involved in numerous disease areas such as tumour metastasis, rheumatoid arthritis, multiple sclerosis and coronary heart disease. Recently, the ancorinoside natural products were described as micromolar MMP inhibitors. Chapter one describes the synthesis of an array of tetramic acids, the core functional group present in the ancorinosides. The compounds synthesised were then tested in biological assays in order to determine whether any were effective MMP inhibitors. The use of molecular modelling technology in aiding the synthesis of tetramic acids is discussed. In chapter two, keto-pyrrolidinones are introduced as an alternative scaffold to tetramic acids. A series of keto-pyrrolidinones was prepared and tested for MMP activity. The third chapter of my thesis describes synthetic studies directed towards ageladine A, a recently isolated MMP inhibitor. The synthesis of the structure reported for ageladine A was achieved via a Suzuki coupling of the pyrrole and pyridine portions. Analogues of this have been tested for MMP activity.