| The development of an interrupted Ugi reaction and its application to the synthesis of methoxy mitragynine pseudoindoxyl are described. The first chapter of this thesis provides an introduction of mitragynine and related natural products. The biochemical relationships of indole, indoxyl, and oxindole alkaloids are described and a general synthetic strategy for mitragynine pseudoindoxyl is discussed. Previous synthetic efforts for spiro-indoxyl compounds including biomimetic transformations of indole alkaloids to indoxyls are described in the second chapter. For studies on the interrupted Ugi reaction, its evaluation for preparing a number of 3-aminoindoles and indoxyls is discussed along with background information on isocyanide based multicomponent reactions. Additionally, asymmetric approach for the synthesis of indoxyls is discussed. The final chapter describes (1) the synthetic strategy for mitragynine pseudoindoxyl (late Ugi and early Ugi approaches), (2) previous synthesis of mitragynine and mitragynine pseudoindoxyl in the literature, (3) nickel mediated reductive cyclization of enynes, (4) completion of a synthesis of methoxy mitragynine pseudoindoxyl. |
