Synthetic polymers are a cause for the high standard of living experienced today. They play a vital role in numerous industries, including packaging, coatings, transportation, and pharmaceuticals. However, the majority of industrial polymers are derived from fossil-based sources and persist in the environment, making waste management difficult and harmful. Consequently, there is strong interest in developing novel polymers from renewable resources with controlled degradability. There are already synthetic polymers like poly(lactic acid) (PLA), which can be synthesized from bio-based sources and exhibit degradable characteristics. However, PLA is synthesized using cationic or coordination-insertion ring-opening polymerization (ROP) techniques, which require monomers with polarized functional groups and demanding reaction conditions. Alternatively, radical polymerization of vinyl monomers is rapid and robust, enabling the synthesis of diverse polymer structures. Yet, most polymers synthesized from this technique have very stable, carbon-carbon backbones which prolong their persistence. To overcome this issue, vinyl monomers that bear an exocyclic methylene group may undergo ring-opening to introduce cleavable functionalities in the polymer backbone in a process called radical ring-opening polymerization (rROP). Cyclic ketene acetals (CKAs) are particularly suitable monomers for rROP, as they undergo ring-opening to introduce cleavable ester groups into the polymer backbone. CKAs are the most well-studied monomers that undergo rROP and are synthesized from a wide range of diols, allowing for structural variety in the resulting polymers. CKAs have successfully been copolymerized with numerous vinyl monomers underscoring their significance a means toward degradable polymers. Despite their potential, CKAs have some challenges, including high polymerization temperatures, long reaction times, and the use of fossil-based reagents and solvents. To address these limitations and explore wood-based diols as suitable alternatives, we aimed to develop novel CKA monomers from α-pinene-derived diols toward degradable and bio-based polymers.