Frame-Shifted Synthesis of Oligoheterocycles as a Platform for Molecular Design

Chemists continue to develop strategies that leverage abundant feedstocks to accelerate the production of medicines, agrochemicals, and materials. Oligoheterocycles are a broad class of molecules that span these disciplines. Cross-coupling strategies are commonly used to assemble oligoheterocycles; however, these methods can be challenging and often rely on precious metal catalysts and building blocks whose production entails significant environmental and economic costs. We present a strategy for the iterative construction of oligoheterocycles that leverages sustainable building blocks designed around high-oxidation-state carbon. By utilizing feedstocks from the base of the chemical supply chain, we generate bifunctional building blocks that chemoselectively engage with a variety of partners through simple condensation manifolds. This approach has enabled the creation of novel scaffolds previously inaccessible by conventional means, exemplifying sustainable design strategies.