May, Aaron Elijah2010-10-222010-10-222010-07https://hdl.handle.net/11299/95246University of Minnesota Ph.D. dissertation. July 2010. Major: Chemistry. Advisor: Thomas R. Hoye. 1 computer file (PDF); x, 234 pages.The bulk of the work done in this thesis falls into the categories of studying acylketene intermediates and developing strategies toward the synthesis of lyngbyaloside B. In the first chapter, a model system of lyngbyaloside B and lyngbouilloside was created to study the dual macrolactonization/pyran-hemiketal formation reaction. In the second chapter, methods for the efficient creation of acylketene intermediates at room temperature were advanced. In the third chapter, the selectivity of additions to acylketene was explored. In the fourth chapter, an aldol method useful to the synthesis of lyngbyaloside B was explored, leading to the discovery of a novel decarboxylative isomerization, which was also explored. In the fifth chapter, progress toward the total synthesis of lyngbyaloside B is presented. Lastly, the sixth chapter involves studies that do not cleanly fit into the previous 5 chapters.en-USAcylketenesLactonizationLyngbyalosideChemistryThesis or Dissertation