Macromolecules have been the targets of the synthetic efforts of investigators, largely because of their widespread applications related to their medicinal, insecticidal and/or phytotoxic properties. Accordingly, we endeavored to synthesize a new series of macrocyclic systems as possible candidates in the development of New Chemical Entities for Drug Discovery Research. Thus, stable macrolactones and macrolactams have been synthesized from substituted phenylalkanoic acid systems in modest yields, employing the Ring Closing Metathesis strategy in the macrocyclization steps.