Synthetic Strategies Toward Heterocyclic Seven Membered Ring Systems: Building Libraries of Privileged Scaffolds for Medicinal Chemistry and Forensic Analysis
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Parker, Ariel N.
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Abstract
Natural products are often the inspiration for many pharmaceutical compounds as they are found to have drug-like properties. Many times, these compounds exhibit structural commonalities and are therefore referred to as “privileged structures.” Synthetic organic chemists have devoted significant time and effort into developing efficient methods to access these privileged scaffolds for the construction of diverse libraries. This thesis explores novel synthetic strategies to access the privileged scaffolds: cyclohepta[b]indole and the 1,4-benzodiazepine, flubromazepam. The protocols designed to access these heterocyclic seven-membered ring systems include: 1) a formal [5+2] cycloaddition between alkenes and indole fused alkylidenes, 2) a Friedel-Crafts transformation and 3) a nucleophilic arylation. Additionally, through the development of these modular protocols new discoveries were made providing new insights in medicinal chemistry and forensic analysis.
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2021-12-14
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Dissertation