A primary interest in the Wooley laboratory is the production of functional polymers from renewable sources that are capable of reverting to those natural products once their purpose has been served.  A long-standing focus has been the development of synthetic methodologies that transform sugars, nucleic acids, amino acids and other natural products into polymer materials.  That interest began with motivation toward biomedical materials that could replace metals or degradable aliphatic polyesters in orthopedic repair applications, which turned to the Plant Kingdom’s major structural material, cellulose as a model and inspiration for innovative polymer materials design.  With the intention of constructing polymers that would possess similar mechanical properties to bone while undergoing hydrolytic degradation without requiring cellulase enzymes and with appropriate degradation kinetics that led to bioabsorbable degradation products, the initial concept involved replacing glycosidic linkages by installation of carbonates between the glucose repeat units.  The initial synthetic target, therefore, was a poly(glucose carbonate).  Since then, this concept has been expanded significantly, and many synthetic approaches have been developed that have afforded a breadth of sustainable, degradable polymers derived from natural products as building blocks. The inherent diversities of natural products provide opportunities to expand the scopes, complexities and properties of polymers, by utilizing fundamental organic chemistry approaches.  This presentation will provide historical perspectives of Wooley’s journey toward sustainable polymer chemistry and its ultimate translation to carbohydrate-derived plastics commercially.  It will also reflect upon the future of polymer materials, with particular emphasis on sourcing of feedstocks and in-built degradability and digestibility to address sustainability, and with interests in the design of next-generation plastics that meet important societal needs while allowing for dynamic reconfigurability and avoiding health, welfare, and environmental adversities.