Synthesis and Applications of Cyclobutenes

Our group is interested in cyclobutene analogs of fatty acids as reactive coatings, potential antibiotics, and as a new class of bioconjugate linkers. A convenient synthesis of this class of molecules was previously reported from our lab. However, ammonia, a key reagent in the earlier route, was recently reclassified as a highly corrosive gas requiring highly specialized equipment for storage and handling. The goal of this research was to find a convenient synthesis for the formation of cyclobutene that did not involve the use of ammonia. The other part of this thesis describes the preparation of a short chain cyclobutene fatty acid as a substrate for conjugation to an amino acid as part of a collaboration targeting the synthesis of proteins, which could be selectively modified using the cyclobutene/tetrazine click reaction. Advisor: Patrick H. Dussaul