Approach to Tetrodotoxin via the Oxidative Amidation of a Phenol.

An approach to tetrodotoxin that relies on the oxidative amidation of methyl 4-hydroxyphenylacetate as a key step is described. The stereoselective introduction of a β-hydroxynitrile functionality on one of the double bonds of the emerging dienone is achieved through an intramolecular nitrile oxide cycloaddition−fragmentation sequence. [ABSTRACT FROM AUTHOR]