With regards to the proposed simplifying C-H amination disconnection, a variety of approaches were evaluated. Despite dozens of studies towards the STX family, this type of transformation was not known . Direct C-H oxidation approaches were unselective or led to complex mixtures . Electrochemical oxidation led only to Shono-type products such as 25 that proved recalcitrant to productive downstream functionalization. Attempts to dehydrate the secondary alcohol followed by oxidation were met with failure as the dehydration attempts led only to decomposition (26). Inspired by Nagasawa's use of hypervalent iodine oxidants, IBX-based oxidation was attempted leading to a-hydroxy enone 27 in ca. 20% yield after extensive optimization . Building on this outcome, a range of I-based oxidants and conditions were evaluated before discovering that PIFA could deliver the desired cyclized adduct 28 ; further optimization of this hit resulted in a robust and scalable solution to forge this critical N-C skeletal bond.