Project Abstract Nitrogen-containing heterocycles are ubiquitous in biologically active natural products and drug agents and are found within 59% of FDA-approved human therapeutics. Novel N-heterocyclic natural products are potentially important drug leads toward the treatment of human disease and new green synthetic methodology for their laboratory synthesis are critically needed toolsets. This proposal merges the expertise of four independent laboratories toward the goals of identifying novel N-heterocyclic natural products and generating new electrosynthetic strategies toward their laboratory synthesis. The Jeffrey Laboratory (UNR) is executing targeted metabolomics acquisitions and analyses in order to isolate and structurally characterize novel N-heterocyclic natural products. The Chain Laboratory (UD) is developing electrosynthetic strategies toward the total syntheses of these new natural products and the development of new electrochemical methodologies. The Hernandez– Pagan Laboratory (UD) is generating an array of metal nanoparticle materials that will facilitate new electrochemical bond-forming reactions toward our syntheses of N-heterocyclic materials. The Davidson Laboratory (UD) will leverage machine learning and data-enabled approaches to systematically navigate the vast number of potentially influential synthetic parameters during nanoparticle synthesis and electrosynthetic tranformations to guide the development of sustainable synthetic approaches to N-heterocyclic natural products.