Gilbertson, Scott R.2019-05-23August 2012018-08August 201https://hdl.handle.net/10657/3998The synthesis of the compounds with medium-sized rings, especially those with a 5,8-fused ring system embedded into the structure, had long been pursued due to their ubiquitousness in numerous natural products and pharmaceutical molecules. These rings could be efficiently synthesized using metal-catalyzed higher order cycloaddition. In our studies, a previously-reported Rh-catalyzed [4+2+2] cycloaddition was developed and optimized to generate fused systems with a cyclooctadiene core from allenedienes and external alkynes. Upon screening of various metal complexes, ligands and solvents, a rhodium-BozPHOS complex was found to have the best reactivity. This cycloaddition between allenedienes and alkynes showed moderate yield and good substrate tolerance, showing good synthetic potential.application/pdfengThe author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).AllenedieneCycloaddition5,8-fused ringsBozPHOSRh-catalyzed2019-05-23Thesisborn digital