Groess, Leah2017-03-142017-03-142016-12https://hdl.handle.net/11299/185173University of Minnesota Ph.D. dissertation.December 2016. Major: Chemistry. Advisor: Wayland Noland. 1 computer file (PDF); vii, 170 pages.Many compounds containing an indole ring system have important biological and chemical significance. There are several biologically active indole-containing natural products as well as synthetic products and many indole-containing compounds have pharmaceutical applications. Research is being done to find new methods of synthesizing indole compounds with the goal of developing pathways towards natural products as well as providing access to potential anticancer drugs. The Diels-Alder reaction using vinylpyrroles is an efficient and often high-yielding way to make the indole ring system as well as setting the stereochemistry. While most Diels-Alder products from vinylpyrroles rearrange to reform the aromatic pyrrole ring, reaction of N-tosyl-2-vinylpyrrole with dienophiles gives an unrearranged Diels-Alder adduct. The unrearranged adduct is stable enough to be isolated and stored but is reactive enough to undergo other reactions, potentially leading to new compounds. One such case is the hydroperoxidation of the Diels-Alder adduct, when it reacts readily with oxygen from the air to form an autoxidation product. This pathway is being explored as a way to increase the functionality and variety of compounds potentially available.enAlderDielsvinylpyrroleThesis or Dissertation