Formal Synthesis of (±)-Tetrodotoxin via the Oxidative Amidation of a Phenol: On the Structure of the Sato Lactone.
A formal total synthesis of (±)-tetrodotoxin that relies on the bimolecular oxidative amidation of a phenol is described, and a structural correction of the Sato lactone, an important tetrodotoxin intermediate, is provided. This work lays the foundation for an ultimate enantioselective synthesis.
Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.
Sanjia
S
Xu
Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.
Marco A
MA
Ciufolini
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D007783:Lactones; D010636:Phenols; D013779:Tetrodotoxin