Efficient Synthesis of Polyaromatic Hydrocarbon via a Formal [2+2] Cycloaddition.
A potassium base-promoted formal [2+2] cycloaddition of 2-acyl-2'-vinyl-1,1'-biaryls was developed to afford benzo-fused polycyclic cyclobutanols in a highly stereoselective manner. We demonstrated synthesis of substituted polycyclic aromatic hydrocarbons and these heterocyclic derivatives via this cyclization, followed by an acid-promoted rearrangement. Furthermore, asymmetric total synthesis of phenanthroindolizidine alkaloid (-)-tylophorine was achieved using our methodology and late-stage asymmetric hydrogenation of a cyclic imine.
Graduate School of Pharmaceutical Sciences, Kyoto University.
Yousuke
Y
Yamaoka
D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D061565:Cycloaddition Reaction / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006865:Hydrogenation; D007212:Indolizines / Q000138:chemical synthesis*; D010616:Phenanthrenes / Q000138:chemical synthesis*; D010618:Phenanthrolines / Q000138:chemical synthesis; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*
D000470:Alkaloids; D006571:Heterocyclic Compounds; D007212:Indolizines; D010616:Phenanthrenes; D010618:Phenanthrolines; D011084:Polycyclic Aromatic Hydrocarbons; C521640:phenanthroindolizidine; C004218:tylophorine