화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.138, No.10, 3298-3301, 2016
Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid
Described herein is a catalytic asymmetric total-synthesis of (-)-actinophyllic acid, with the key step being a chiral phosphine-catalyzed [3 + 2] annulation between an imine and an allenoate to form a pyrroline intermediate in 99% yield and 94% ee. The synthesis also features CuI-catalyzed coupling between a ketoester and a 2-iodoindole to shape the tetrahydroazocine ring; intramolecular alkylative lactonization; SmI2-mediated intramolecular pinacol coupling between ketone and lactone subunits to assemble the complex skeleton of (-)-actinophyllic acid; and an unprecedented regioselective dehydroxylation.