This thesis addresses fundamental scientific questions such as: How are complex natural products synthesized in vivo? Can we replicate these conditions in a laboratory environment? What is the biological function of such secondary metabolites? What are the biological origins of chirality? These issues are explored in an accessible manner using a multidisciplinary approach spanning chemistry, biology and physics to investigate an interesting family of complex natural products isolated from marine molluscs – the tridachiahydropyrones. The work has achieved: Elegant biomimetic syntheses of a number of the tridachiahydropyrone compounds in vitro using organic synthesis techniques The characterization of the interactions between these compounds and a range of model membrane systems using a series of fluorescence spectroscopic studies The investigation of the antioxidant and photoprotective properties of the compounds by means of biophysical assay techniques The synthesis of tridachiahydropyrone utilizing the model membrane systems as biomimetic reaction media.