Tagged: diversity oriented synthesis
Congratulations to Lauren Brown, Mikayo Hayashi and Professor John Porco on their recent Communication in the European Journal of Organic Chemistry entitled “Asymmetric Dearomatization/ Cyclization Enables Access to Novel Chemotypes.”
Abstract: Enantioenriched, polycyclic compounds were obtained from a simple acylphloroglucinol scaffold. Highly enantioselective dearomatization was accomplished using a Trost ligand palladium(0) complex. A computational DFT model was developed to rationalize observed enantioselectivities and revealed a key reactant-ligand hydrogen bonding interaction. Dearomatized products were used in visible light-mediated photocycloadditions and oxidative free radical cyclizations to obtain novel polycyclic chemotypes including tricyclo[4.3.1.01,4]decan-10-ones, bicyclo[3.2.1]octan-8-ones and highly-substituted cycloheptanones.