Celebrating Scholarship and Creativity Day (2018-)

Document Type

Paper

Publication Date

4-25-2019

Advisor

Thomas Jones, Chemistry

Abstract

Janolusimide A, and its analogue Janolusimide B, are natural marine tripeptide toxins that act as cholinergic agents and are thus effective antifeedants. Their neurotoxic activity is shown to be antagonized by atropine suggesting an inhibition interaction with acetylcholine receptors and is consequently a potential pesticide. This research project consists of developing conditions for the synthesis of the dipeptide aldehyde fragment in Janolusimide using a Weinreb amide reduction approach. Previous syntheses of Janolusimide required an expensive organoborane catalyst and several synthetic steps. Our process via the Weinreb amide is likely to produce the desired compound in a shorter synthetic process. Progress on this project is still ongoing through optimizing reduction conditions for the Weinreb amide. Future use of the finished product can range from advancement of its enantiomers and their chemical effects to use as a pesticide.

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