Friedel-Crafts Reactions to Construct the Core of Flinderole C
Presentation Type
Poster
Full Name of Faculty Mentor
Bryan Wakefield, Chemistry
Major
Biochemistry
Presentation Abstract
Flinderoles C, isolated from plants of the Flindersia genus, is a new class of antimalarial bisindole alkaloids that have antimalarial activity. Indoles and indole-containing compounds such as flinderoles A-C are important components of natural products and the pharmaceutical industry. Flinderole C is reported to be the most active, thus its synthesis is being explored in the laboratory. The purpose of these laboratory experiments is to make progress toward efficiently synthesizing flinderole C. The 1,2-pyrroloindole is a key structural component of these molecules that have been successfully synthesized by our group. Our previous approach revolved around a cross-metathesis to produce an indole tethered to an allylic alcohol. In the lab, BF3•OEt2 and diphenyl phosphate-catalyzed Friedel-Crafts reactions have been shown to give access to the central ring system found in the flinderoles. These reactions have proven difficult to optimize in part due to low yielding synthesis of the allylic alcohol. We hope that the new route to the necessary alcohol will provide access to larger quantities of the cyclization precursor to allow us to find the optimal conditions for the Friedel-Crafts transformation.
Start Date
12-4-2023 4:00 PM
End Date
12-4-2023 6:00 PM
Disciplines
Biochemistry | Chemistry
Recommended Citation
Gentile, Christina and Disselkoen, Sadie, "Friedel-Crafts Reactions to Construct the Core of Flinderole C" (2023). Undergraduate Research Competition. 90.
https://digitalcommons.coastal.edu/ugrc/2023/fullconference/90
Friedel-Crafts Reactions to Construct the Core of Flinderole C
Flinderoles C, isolated from plants of the Flindersia genus, is a new class of antimalarial bisindole alkaloids that have antimalarial activity. Indoles and indole-containing compounds such as flinderoles A-C are important components of natural products and the pharmaceutical industry. Flinderole C is reported to be the most active, thus its synthesis is being explored in the laboratory. The purpose of these laboratory experiments is to make progress toward efficiently synthesizing flinderole C. The 1,2-pyrroloindole is a key structural component of these molecules that have been successfully synthesized by our group. Our previous approach revolved around a cross-metathesis to produce an indole tethered to an allylic alcohol. In the lab, BF3•OEt2 and diphenyl phosphate-catalyzed Friedel-Crafts reactions have been shown to give access to the central ring system found in the flinderoles. These reactions have proven difficult to optimize in part due to low yielding synthesis of the allylic alcohol. We hope that the new route to the necessary alcohol will provide access to larger quantities of the cyclization precursor to allow us to find the optimal conditions for the Friedel-Crafts transformation.