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Poly(lactic acid) (PLA) offers a renewable and degradable alternative to petroleum-based plastic, but its mechanical properties are not ideal for many applications. Herein, we describe the synthesis and polymerization of oxo-3,8-dioxabicyclo[3.2.1]octane (ODO), a bio-derived bicyclic lactone, and show that copolymers of L-lactide (LA) with small amounts of ODO have improved mechanical properties over PLA. Homopolymerization of ODO to poly(oxo-3,8-dioxabicyclo[3.2.1]octane) (PODO) is optimized for both solution-phase, organocatalytic and melt-phase, metal-catalyzed conditions. In comparison to the monocyclic analog, ε-caprolactone (CL), ODO has a lower enthalpy of polymerization and faster rate of polymerization. PODO is an amorphous, elastomeric polyester that has a 90 °C higher Tg than poly(ε-caprolactone) (PCL). Statistical copolymerization of LA with small fractions of ODO yields tough and transparent thermoplastics that have over 12× elongation at break compared to native PLA, while maintaining Tg, Young’s modulus (E), and yield strength. Together, these results describe how the incorporation of the tetrahydrofuran ring alters polymerizability and the thermomechanical properties of the homopolymer and copolymer materials.