Effective utilization of a wide spectrum of naturally abundant compounds is a vital strategy in achieving sustainability in the chemical industry. Herein, we demonstrate a proof of concept that enables the transformation of naturally occurring phenyl propene derivatives (e.g., Eugenol, Safrole) to valuable aromatic aldehydes (e.g., Vanillin, Piperonal) by means of two different strategies. The common denominator between these two methods is the effective one-pot coupling of a chemical (Strategy A. Wacker-Oxidation or Strategy B. catalytic isomerization) and an enzymatic transformation (Strategy A. three-step enzymatic cascade or Strategy B. one-step enzymatic “shortcut” transformation). The enzymatic cascade reaction (Strategy A) is realized by the combination of a Baeyer-Villiger-Monooxygenase (TmCHMO) together with an Esterase (PFE_I) and an alcohol dehydrogenase (AlkJ). For the “shortcut” enzymatic transformation (Strategy B) a coenzyme free aromatic dioxygenase (ADO) is employed [1]. Both strategies were realized in a one-pot fashion and yielded the desired aldehydes in good to very good yields. [1] J. Ni, Y.-T. Wu, F. Tao, Y. Peng, P. Xu, A coenzyme-free biocatalyst for the value-added utilization of lignin-derived aromatics, J. Am. Chem. Soc. 2018, 140, 16001-16005, doi: 10.1021/jacs.8b08177