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 beta-hydroxynitrile functionality on one of the double bonds of the emerging dienone is achieved through an intramolecular nitrile oxide cycloaddition-fragmentation sequence.
Mendelsohn
Brian A
BA
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.
Ciufolini
Marco A
MA
D000577:Amides / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry; D010084:Oxidation-Reduction; D019800:Phenol / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013779:Tetrodotoxin / Q000737:chemistry*
D000577:Amides; D009570:Nitriles; D019800:Phenol; D013779:Tetrodotoxin