SYNTHESIS OF PHENYL ANALOGUES REPLACING THE OXADIAZOLE RING OF PHIDIANIDINES
Presentation Type
Event
Full Name of Faculty Mentor
Bryan Wakefield
Major
Chemistry
Presentation Abstract
Phidianidine analogues have been found to provide protection from nerve damage caused by reactive oxygen species (ROS) which can contribute to Alzheimer's disease. The synthesis of phidianidine analogues could lead to more effective compounds to prevent oxidative nerve damage and provide a better understanding of the mode of action. In previous syntheses have relied on constructing the central 1,2,4-oxadiazole ring to combine the indole and biaryl side chain which limits the types of analogues that can be constructed. However, the synthetic approach we are employing relies on Pd cross-coupling which will enable the 1,2,4-oxadiazole ring to be replaced and the importance of each individual atom on the ring to the determined. And this approach will also enable substituted indoles to be added in the final step so new derivatives can be constructed quickly. The synthesis of analogues that replace the oxadiazole with a phenyl ring is ongoing. The synthesis consists of two cross-coupling reactions, a selective bromination, and reduction to provide an alcohol. This alcohol is the key intermediate needed for the introduction of indole rings and the completion of the synthesis.
Course
Chemistry 499
External Presentation
1
Location
Lib Jackson Student Union, Atrium
Start Date
16-4-2019 12:30 PM
End Date
16-4-2019 2:30 PM
Disciplines
Chemistry
Recommended Citation
Leake, Kadarius, "SYNTHESIS OF PHENYL ANALOGUES REPLACING THE OXADIAZOLE RING OF PHIDIANIDINES" (2019). Undergraduate Research Competition. 30.
https://digitalcommons.coastal.edu/ugrc/2019/poster/30
SYNTHESIS OF PHENYL ANALOGUES REPLACING THE OXADIAZOLE RING OF PHIDIANIDINES
Lib Jackson Student Union, Atrium
Phidianidine analogues have been found to provide protection from nerve damage caused by reactive oxygen species (ROS) which can contribute to Alzheimer's disease. The synthesis of phidianidine analogues could lead to more effective compounds to prevent oxidative nerve damage and provide a better understanding of the mode of action. In previous syntheses have relied on constructing the central 1,2,4-oxadiazole ring to combine the indole and biaryl side chain which limits the types of analogues that can be constructed. However, the synthetic approach we are employing relies on Pd cross-coupling which will enable the 1,2,4-oxadiazole ring to be replaced and the importance of each individual atom on the ring to the determined. And this approach will also enable substituted indoles to be added in the final step so new derivatives can be constructed quickly. The synthesis of analogues that replace the oxadiazole with a phenyl ring is ongoing. The synthesis consists of two cross-coupling reactions, a selective bromination, and reduction to provide an alcohol. This alcohol is the key intermediate needed for the introduction of indole rings and the completion of the synthesis.