α-N-phthalimido-oxy isobutyrate-mediated deoxygenative arylation: total synthesis of alanenses A and B

Abstract

Inspired by a biosynthetic hypothesis of 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. The other approach involves 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, B, and O7′-methyllacinilene E.