α-N-Phthalimido-Oxy Isobutyrate-Mediated Deoxygenative Arylation: Total Synthesis of Alanenses A and B

Inspired by our biosynthetic hypothesis for alanense A, we developed two distinct methods for the deoxygenative arylation of α-N-phthalimido-oxy isobutyrate (NPIB), derived from hydroxyl groups adjacent to or conjugated with a carbonyl moiety. One approach utilizes photoredox catalysis to achieve a radical-mediated arylation reaction. Alternatively, we designed an acid-mediated arylation method that proceeds through a cationic intermediate. The acid-mediated approach was successfully applied to the total syntheses of alanenses A and B, as well as O7′-methyllacinilene E.