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A Diels-Alder Approach to Indoles and Carbazoles: Hallucinogens, Antivirals and Parkinson's Drugs

Gary Points (Beaudry Group) - Chemistry Thesis Defense

Aromatic heterocycles are core structural motifs in natural products, pharmaceuticals and biological polymers. Indoles, in particular, represent a significant subclass of aromatic heterocycles, both in terms of sheer numbers, but also in biological and pharmaceutical relevance. As such, new methodologies for the synthesis of indoles represent an important and continually growing field in organic chemistry.

This work will explore new strategies for the synthesis of substituted indoles and carbazoles from alkyne bearing 2-pyrones. These substrates undergo base catalyzed Diels-Alder-retro-Diels-Alder reactions, forging the bicyclic indole or tricyclic carbazole ring systems. Using this strategy, many previously difficult to synthesize 4-substituted indoles were readily prepared. A variety of di- and tri- substituted indoles and carbazoles were also prepared with control of regiochemistry.

The utility of this methodology was further highlighted in the syntheses of ergot alkaloid lysergic acid and the carbazole natural product clausine C. Finally, using this method in combination with other synthetic strategies, we prepared 12 ropinirole analogues, with systematic substitution of 4 different functional groups around the benzene portion of the indole ring. These analogues will be screened in dopamine and serotonin receptor binding assays. We plan to assess the impact of binding affinity and receptor subtype selectivity related to functional group manipulation on a known dopamine agonist.   

Thursday, December 1 at 1:00pm

Kidder Hall, 274
2000 SW Campus Way, Corvallis, OR 97331

Event Type

Lecture or Presentation

Event Topic

Research

Audience

Faculty and Staff, Student, Alumni, Industry Partner, Online

County

Benton

Tags

Defense

Organization
College of Science, Department of Chemistry
Contact Name

Gary Points

Contact Email

gary.points@oregonstate.edu

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