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
Date of Graduation
Eberly College of Arts and Sciences
Bjorn C G Soderberg
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 Soderberg variety of this methodology has been utilized to synthesize several asymmetric tryptophan derivatives along with a collection of 2- and/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".
Dacko, Christopher Andrew, "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" (2009). Graduate Theses, Dissertations, and Problem Reports. 4454.