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Part I: Synthesis Of Pyrrolo[1,2-A]Indoles Part Ii: Studies Towards Arboflorine, Michael B. Johansen

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Part one of this thesis focuses on the synthesis of pyrrolo[1,2-a]indoles from nitrones and 1,1-cyclopropanediesters, by way of tetrahydro-1,2-oxazines. A five step synthetic sequence through tetrahydro-1,2-oxazine synthesis, intramolecular Heck reaction, Krapcho dealkoxycarbonylation, reductive N-O bond cleavage, and acid catalyzed transannular alcohol displacement, is developed to access the desired pyrrolo[1,2-a]indoles. Part two of this thesis details the functionalization of indoles by installation of a malonate moiety, by means of copper catalyzed carbenoid reactivity. A wide range of malonyl indoles with varying substitution patterns is shown to be accessible through the developed method. The final chapter focuses on the application of this …