| This dissertation will describe the development and application of novel methods for heterocycle synthesis. The first chapter will outline the development of a titanocene catalyzed epoxide-opening rearrangement to prepare indolines from epoxyanilines. A discussion of the reaction development, along with the substrate scope and limitations will be reported.;The second chapter will describe progress toward expanding the scope of a Staudinger/aza-Wittig reaction used to prepare substituted 1,2,4-triazines. This methodology has been applied towards the synthesis of a model system for the DEF rings of the natural product noelaquinone. The challenges associated with the Staudinger/aza-Wittig reaction, and the late-stage oxidation strategy to prepare the DEF rings of the noelaquinone model system will be discussed.;The third chapter will describe the importance and general preparation of (E)-alkene peptide isosteres. Using compounds prepared in the UPCMLD and published on PubChem as a reference, we present our ongoing initiative to expand the library of alpha,beta-cyclopropyl-gamma-amino acid analogs. |
