The synthesis of tryptophan derivatives, 2- and/or 3-substituted indoles, progress toward dilemmaones A-C, and synthetic studies towards fistulosin via palladium-catalyzed reductive N-heteroannulation

Abstract

Palladium-catalyzed carbon monoxide-mediated reductive N-heteroannulation of o-nitrostyrenes has emerged as a very powerful method for constructing the corresponding indole core. The Söderberg variety of this methodology has been utilized to synthesize several asymmetric tryptophan derivatives along with a collection of 2and/or 3-substituted indoles. The same protocol has also been employed to make synthetic progress toward the construction of the marine indole alkaloids Dilemmaones A-C. Finally, this versatile cyclization was implemented in studies designed to determine the true structure of the compound isolated by Tomita et. al. and given the name "fistulosin". iii Acknowledgments This work is dedicated to my grandparents, Andrew and Helen Dacko, and also to my good friend Jon Murt, all of whom passed away during my time as a graduate student at West Virginia University. I miss them all very dearly and wish they could have been here to witness my accomplishments. I would like to thank my advisor, Dr. Björn Söderberg, for his constant guidance, patience, and friendship during my graduate studies. I owe my development as a chemist to his counseling and support. I would also like to thank the faculty members in the C.