Author ORCID Identifier
Semester
Fall
Date of Graduation
2023
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Björn Söderberg
Committee Member
Margaret Hilton
Committee Member
Mark McLaughlin
Committee Member
Carsten Milsmann
Committee Member
Brian Popp
Abstract
A novel, base-mediated cyclization was developed to form N-hydroxy- and N-alkoxyindoles from 2-(2-nitrophenyl)butenoates. Potassium tert-butoxide or sodium tert-pentoxide, with or without the in-situ addition of an electrophile, formed a multitude of N-hydroxy- and N-alkoxyindoles. The formation of these butanoate precursors was improved via a Barluenga coupling reaction. Novel 4,5,6,7-tetramethoxy-1,10-phenanthroline was utilized as an ancillary ligand within the Watanabe-Cenini-Söderberg reductive cyclization reaction conditions. These new reaction conditions produced high yields for sterically hindered 2-nitrostyrenes and the first synthesis of dilemmaone A using this reductive cyclization. Racemosin B was synthesized in a three-step process utilizing a Suzuki coupling reaction, followed by the improved WCS reductive cyclization conditions. Substitutions to the terphenyl precursor structure were made, allowing for possible substituted racemosin B analogs.
Recommended Citation
McClay, Blaine Thomas, "Investigations into Indole Formation: Base-mediated Formation of N-hydroxy- and N-alkoxyindoles, Ancillary Ligand Development for Watanabe-Cenini-Söderberg Cyclization, and Total Synthesis of Racemosin B" (2023). Graduate Theses, Dissertations, and Problem Reports. 12279.
https://researchrepository.wvu.edu/etd/12279
Embargo Reason
Publication Pending