The renewed interest in troponoid compounds as potential therapeutic agents and the ongoing discovery of new, naturally-occurring and biologically active members of the class has resulted in an attendant focus on developing and deploying methods for their synthesis. This review highlights some of the significant recent developments in the area of troponoid chemistry that serve to contextualize our group’s longstanding and ongoing interest in the synthesis of such compounds through the cyclopropane-mediated ring-expansion of cyclohexanoid and benzenoid compounds. The various means by which such conversions can be accomplished and their application to the synthesis of both natural and non-natural troponoids are detailed.