Optimization of Indole Additions to Aromatic Aldehydes for the Synthesis of Phidianidine Analogues
Presentation Type
Event
Full Name of Faculty Mentor
Bryan Wakefield
Major
Chemistry
Presentation Abstract
Nature provides a plethora of substances that can be useful in battling diseases that afflict the human population. Phidianidine, which was isolated from a marine opisthobranch mollusk, is one such substance that has been found to have various biological activities. Analogues of this molecule have been shown to have protective effects on nerve cells that could be damaged by Alzheimer's and other neurodegenerative diseases. The molecule contains a 1,2,4-oxadiazole ring, which other groups have used to combine the two halves of the molecule to complete the synthesis. While this approach is well suited to the synthesis of phidianidine, it does not lend itself to the construction of diverse analogues. We have developed a synthetic approach where the indole moiety is added late-stage to an alcohol or aldehyde that allows the indole portion of the phidianidine molecule to be easily modified. This project is focused on finding the conditions needed to add indoles to phidianidine derived aromatic aldehydes in high yields.
Course
CHEM 499
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
Altman, Katherine, "Optimization of Indole Additions to Aromatic Aldehydes for the Synthesis of Phidianidine Analogues" (2019). Undergraduate Research Competition. 2.
https://digitalcommons.coastal.edu/ugrc/2019/poster/2
Optimization of Indole Additions to Aromatic Aldehydes for the Synthesis of Phidianidine Analogues
Lib Jackson Student Union, Atrium
Nature provides a plethora of substances that can be useful in battling diseases that afflict the human population. Phidianidine, which was isolated from a marine opisthobranch mollusk, is one such substance that has been found to have various biological activities. Analogues of this molecule have been shown to have protective effects on nerve cells that could be damaged by Alzheimer's and other neurodegenerative diseases. The molecule contains a 1,2,4-oxadiazole ring, which other groups have used to combine the two halves of the molecule to complete the synthesis. While this approach is well suited to the synthesis of phidianidine, it does not lend itself to the construction of diverse analogues. We have developed a synthetic approach where the indole moiety is added late-stage to an alcohol or aldehyde that allows the indole portion of the phidianidine molecule to be easily modified. This project is focused on finding the conditions needed to add indoles to phidianidine derived aromatic aldehydes in high yields.