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.
Comments
Great Poster!
Really impressive!
Presentation Time
I will be presenting from now until 6:30 pm!
Apologies my virtual meeting time was initially entered wrong.
Layout
The poster made good use of space and the important figures were centered where they were most noticeable. Good luck on the future work.