Date of Graduation
2007
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Bjorn C.G. Soderberg
Committee Co-Chair
Kung K. Wang
Committee Member
John. H. Penn
Committee Member
Jeffery L. Petersen
Committee Member
Peter M. Gannett
Abstract
Palladium-catalyzed reductive N-heteroannulation has emerged as a powerful tool in the construction of numerous N-containing heterocycles including indoles. The Soderberg conditions of these reactions have effectively been utilized to synthesize numerous 3-ethoxyindoles, the naturally occurring koniamborine and salviadione. Additionally, this reaction was used to synthesize 2-octadecyl-3-methoxyindole used in the systematic study towards the compound fistulosin, an antifungal compound isolated from the roots of the Welsh onion whose actual structure is in question. 2-(Stearamido)benzoic acid was proposed as a potential structure for the actual compound and was synthesized for ultimate comparison. The data obtained for this compound is in close agreement with the data reported for fistulosin.
Recommended Citation
Clawson, Ronald W., "The synthesis of 3-ethoxyindoles, koniamborine, salviadione and studies toward fistulosin utilizing palladium-catalyzed reductive N-heteroannulation." (2007). Graduate Theses, Dissertations, and Problem Reports. 8642.
https://researchrepository.wvu.edu/etd/8642