Biorefinery may be defined as the process of accessing chemical commodities from living systems; consequently, biomass becomes the antecedent for renewable resources through biorefinery. Advantages to this process over petroleum refinery include: (1) increased potential for sustainable products, (2) increased diversity in chemical structure including heterocycles, and (3) potential for regional resource independence. Despite these clear advantages, adoption of biorefined commodities can be limited by the risk associated with small initial application portfolios and concomitant uncertainties. The strategies adopted by our dynamic and collaborative research team entail continuous engagement of those issues by: (1) preparing renewable polymers, (2) chemical diversification of biomass-derived platform chemicals, (3) direct modification of biopolymers, and (4) development of petroleum replacements. Battling the inveterate proclivity towards portents of gloom need not solely justify investigations into biorenewable feedstock chemicals; the ramifications of bioinspired molecular inquiry create opportunities to go beyond mere sustainability through innovation. This dissertation includes specific examples which illustrate utilization of three types of biomass: (1) oil seeds, (2) lignin, and (3) carbohydrates. Each class of biomass-derived materials offered unique advantages as well as challenges associated with their varied structures. The presentation has been divided into five sections: (1) biomass, sustainable chemistry and design thinking; (2) styrene replacements and their application in renewable vinyl ester thermosets; (3) catalyst-free lignin valorization by acetoacetylation; (4) chemical diversification of 5-(hydroxymethyl)furfural; (5) valorization of cellulose-derivable platform chemicals by cycloaddition with a potentially bioderivable reactive intermediate: benzyne.