Fall Research Expo 2021

Total Synthesis of Carbazole Alkaloids, Clausenawallines D & I

Carbazoles are tricyclic motifs containing a five-membered nitrogen-containing ring fused between two benzene rings which are present in pharmaceuticals and natural compounds. Clausenawallines are a group of carbazole alkaloids that come from the plant species Clausena wallichi that have been found to have anti-microbial properties. Eleven of these clausenawallines have been isolated and classified from A to K. Of these eleven compounds, just clausenawalline D had been synthesized previously in a lab. The potential pharmacological properties generated our interest in synthesizing these compounds. This poster presents the total synthesis of clausenawalline D with an improved yield and the novel synthesis of clausenawalline I. In addition to these total syntheses, we present progress in the synthesis of clausenawalline C. A retrosynthetic analysis was used that approached that generated the carbazole scaffold from 2-choloranilines and aryl bromides via catalytic animation and C-H activations; however, this approach was replaced by Suzuki coupling using boronic acids with nitrobenzene followed by Cadogan cyclization which allowed for greater a greater diversity of products and the relative ease of the cross-coupling reaction. Future work will focus on the synthesis of other clausenawallines and eventually biological evaluation of these compounds. 

 

PRESENTED BY
Other
College of Arts & Sciences 2022
Advised By
Marisa Kozlowski
Professor of Chemistry
Join Julia for a virtual discussion
PRESENTED BY
Other
The Panaphil and Uphill Foundations
College of Arts & Sciences 2022
Advised By
Marisa Kozlowski
Professor of Chemistry

Comments

September 14 | 5:35 PM : by winkler@upenn.edu

Really impressive!

I will be presenting from now until 6:30 pm! 

Apologies my virtual meeting time was initially entered wrong. 

The poster made good use of space and the important figures were centered where they were most noticeable. Good luck on the future work.