In the present work, two approaches were followed in the oxidation of the macrocyclic diene 1,9-cyclohexadecadiene. Firstly, an epoxidation using hydrogen peroxide as oxidant was revised. A set of precursors used to form the peroxotungstophosphate active catalyst and a set of phase transfer catalyst were screened. The conversion and selectivity to the target epoxide varied pending on the precursor and PTC of choice. Secondly, a Wacker-type oxidation was done using different palladium complexes. Among them, a specific type of complexes showed a higher selectivity to the target ketone.