Organic cage chemistry, an incredibly diverse sect of organic synthesis, has alwaysintrigued chemists to push the limits of synthetic knowledge, to explore novel structural elements, and to understand unique reactivity patterns. Organic cage compounds containing oxygen heteroatoms, known as oxacages, have been routinely investigated since the late 1990s as potential analogs to the highly researched crown ethers (and other cryptands) for use in molecular recognition. Crown ethers and cryptands are well known for their exceptional metal-chelation capacity and high affinity for specific metal ions. Oxacages, however, are expected to display different binding patterns and greater selectivity towards specific ions due to being more conformationally ridged. The cage diene 1 is a literature known compound that was initially proposed as a model compound for the elusive bishomohexaprismane 10. Further investigation into this scaffold lead some researchers to probe 1 as a building block for the tetraoxacage 183. While initial attempts to prepare 183 through ozonolysis failed, we recognize the potential synthetic value of diene 1. Utilizing selected functionalization methods, we attempted to prepare tetraoxacage 183 through a multi-step linear synthesis. This would avoid the issues cited with the initial ozonolysis and also provide access to many novel scaffolds that may prove useful in synthesizing other unique and elusive compounds. The preparation of a variety of hydrocarbon, halogenated, and oxygencontaining cages is detailed herein. Utilizing well understood methods such as carbene addition,epoxidation, and cis-dihydroxylation, we prepared multiple novel scaffolds for further investigation into the effects of functionalization on cage systems. These scaffolds were also prepared as potential precursors to elusive and highly sought-after systems such as tetraoxacage183. We also utilized acid catalyzed rearrangements of prepared hydrocarbons and epoxides to target novel scaffolds such as the norpentaasterane 126 and investigated the interesting mechanisms observed.