The first total synthesis of (±)-annosqualine by means of oxidative enamide-phenol coupling: pronounced effect of phenoxide formation on the phenol oxidation mechanism

The first total synthesis of a spiro-isoquinoline alkaloid, (±)-annosqualine, was established by employing an enamide-phenol coupling of an isoquinoline derivative with a hypervalent iodine reagent, as a key step.