The increased consumption of fossil-based consumer products is associated with environmental issues and health hazards. To maintain the same quality of life and comfort offered by fossilbased materials but without compromising the viability of ecosystems and our environment, a transition from the currently implemented linear model of chemical production is urgently needed. Biopolymers show great potential in replacing fossilbased plastics and materials, still at present monomers from biobased renewable resources only cover ∼1-2% of the commercial polymer market. Considering the future population growth and increased demand for chemical products, accelerated generation of high-performance bio-based materials that are recyclable and biodegradable is required. Designing cost-effective, concise, sustainable methods for synthesizing bio-based monomers from selected biomass, generating materials with tunable properties for aimed applications from them, and finding a way for polymer reuse at end-of-life are current challenges that obstruct the full potential of biopolymers. properties. To ensure a circular materials economy, the synthesized polymers should be prone to undergo chemical recycling and enzymatic (bio) degradation, while at the same time showing properties that mimic fossil-based plastics. Accordingly, polyesters from renewable resources have been in focus as they contain bonds cleavable by chemical and enzymatic catalysts. This family of polymers has found important industrial applications in packaging, coatings, clothing, fibers, films, and resins. One main focus in polyester synthesis has up till now been on the A2+B2 type of polycondensation founded on the design and generation of renewable aliphatic and unsaturated diacids from biomass, which are then typically copolymerized with shortchain diols (Figure ). Mecking et al. showed that by extending the alkyl chain length of biomass-derived aliphatic acids significantly by e.g. metathesis, it is possible to generate renewable polyesters with properties that are similar to those of polyolefins . Conversely, the chemical reaction space of renewable diols for performing A2+B2 polymer synthesis is much less explored (Figure ). It has mainly involved linear and branched short-chain alcohols, including ethylene glycol, 1,2butanediol, 1,3-propanediol, and derivatives thereof. We reasoned that by exploring rigid bicyclic terpene-derived diols from biomass, the generation of hydrolyzable polymers with inherent strain, facilitating their chemical recycling, would be possible; while simultaneously allowing for thermal properties that replicate those of common fossil-based polymers due to intramolecular packing interactions stemming from the out-of-the backbone bicyclic system (Figure ). Whereas cyclic bio-based monomers from lignin (monolignols), hemicellulose (furan-based diols), and sugars (e.g. isosorbide) have been explored , the inclusion of a protruding ring system in the polyester backbone has remained to be developed. Multicyclic terpenes have generated a substantial amount of interest in recent years as renewable non-food-based feedstock for the synthesis of bio-based platform chemicals and polymers. Annually, more than 360,000 tons of turpentine is produced as a side product from the pulp and forestry-based industries. α-pinene, β-pinene, 3-carene, and limonene are the main constituents of turpentine oil. Limonene chemistry is studied to an extent and has been applied in the polymer field. Apart from contributing to sustainability, the aliphatic cyclic rings and stereo centers inherent to terpenes can render polymeric materials with structural strength properties. Such steric factors combined with chirality, and the possibility of hydrogen bonding open up a range of applications including biomedical usage. (-)-α-pinene constitutes (47-95%) of turpentine and is a bulky, chiral terpene that shows potential in replacing fossil-based aromatic as well as aliphatic monomers. Without functionalization, the inert backbone of α-pinene restricts it from undergoing polymerization. However, the valorization of α-pinene can render a library of structurally interesting monomers At the same time opening of the bicyclic ring of α-pinene that is key for rigidity can occur during the polymerization of α-pinene-based monomers. Hence the resulting polymers are incompatible with mimicking the properties of commercial fossil-based materials showing elevated thermal stability. Here we maintain the bicyclic ring structure in the polymer by functionalizing (-)-α-pinene into chiral bulky bicyclic bio-based diols and co-polymerizing them with bio-based aromatic and aliphatic diesters. In addition, it is also interesting to investigate the suitability of those polyesters for chemical recycling and enzymatic degradability by capitalizing on the inherent ring strain imposed by the protruding bicyclic entities. We Scheme 1. Synthesis of trans-Hydroxy nopol (HN, 2) and polyesters thereof (10-13) : Scheme 2. Synthesis of trans-Hydroxy myrtenol (HM, 5) and polyesters thereof (14-17) :