UCLA

This dissertation explores synthetic strategies to access structurally-complex hydrocarbons. It opens with a review on different types of geometric distortion present in π-bond-containing functional groups, and how they have been recently used in synthesis. Then a symmetry-based approach toward the total synthesis of dodecahedrane is described. Here, cascading processes for the assembly of dodecahedrane's intricate carbon skeleton are discussed. Following the total synthesis efforts, the synthesis and reactivity of alkenes that feature twisting and pyramidalization is described. A new method for the synthesis of both anti-Bredt olefins and alkenes at ring fusions is developed, providing a means to study these elusive strained intermediates. Finally, a new OLED device synthesis, safety profiling of 2-iodoxybenzoic acid (IBX), and a perspective on the success of UCLA's Organization for Cultural Diversity in Science (OCDS) are reported.