Following the synthesis of the initial acetyl ester, we explored the possibility of extending the scope of the reaction, to create more apolar compounds with increased reactivity (e.g., cytotoxicity towards malignant cells), as previously demonstrated in the literature with similar substrates. Consequently, our methodology was extended to facilitate the esterification of DHLc with vinyl propionate, hexanoate and octanoate. Additionally, vinyl chloroacetate was also tested for two reasons: firstly, to assess the impact of a larger atom in the acyl chain; and secondly, to investigate the introduction of halogens, given their importance in the synthesis of bioactive molecules.