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UBC Theses and Dissertations

A synthetic approach to tetrodotoxin : via oxidative amidation of a phenol Chau, Jaclyn


This dissertation describes synthetic efforts towards tetrodotoxin. Contact with tetrodotoxin brings upon paralytic shellfish poisoning (PSP) for the unfortunate victim. The syndrome can be fatal in extreme cases and symptoms include nausea, numbing of the lips and body, throat constriction, slurred speech, and loss of coordination. Our approach stems from the oxidative amidation of a phenol as a key step. This technology installs a necessary nitrogen-functionality of the natural product at an early stage; ultimately the route was optimized to allow the synthesis to proceed in a practical manner.

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