MeC(O)OOBu-t in 1,2-dichloro-ethane T=80°C; 4 h; Inert atmosphere;

boron tribromide in dichloromethane T=-78 - 20°C; 3 h;

hydrogenchloride in water; acetonitrile T=20°C; 5 h;

boron tribromide in dichloromethane T=-78 - -10°C; 6 h; Inert atmosphere;

1: 5-isopropyl-3-methyl-1,6,7-naphthalenetriol With titanium tetrachloride in diethyl ether; dichloromethane T=0°C; 0.25 h; 2: dichloromethoxy methane T=0 - 20°C; 21 h;

1.1: acetic acid; bromine / 20.25 h / 20 °C / |Cooling with ice 2.1: potassium carbonate / acetone / 15 h / 30 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 2 h / |Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 5.2: 10 h / -78 - -30 °C / |Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 7.1: acetic anhydride; sodium acetate / 2 h / |Reflux 8.1: sodium hydroxide / methanol; water / |Reflux 9.1: potassium carbonate / acetone / 12 h / 20 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 10.2: 10 h / 20 °C 11.1: silver(l) oxide / methanol / 3 h / 20 °C 12.1: potassium carbonate / acetone / 5 h / 20 °C 13.1: dichloromethane / 0.5 h / 20 °C 14.1: lithium hydroxide hydrate / water; tetrahydrofuran / 1 h / 20 °C 15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / |Inert atmosphere View Scheme

1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / |Inert atmosphere 1.2: 8 h / 100 °C / |Inert atmosphere 2.1: acetic acid; bromine / 20.25 h / 20 °C / |Cooling with ice 3.1: potassium carbonate / acetone / 15 h / 30 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 4.2: 2 h / |Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 6.2: 10 h / -78 - -30 °C / |Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 8.1: acetic anhydride; sodium acetate / 2 h / |Reflux 9.1: sodium hydroxide / methanol; water / |Reflux 10.1: potassium carbonate / acetone / 12 h / 20 °C 11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 11.2: 10 h / 20 °C 12.1: silver(l) oxide / methanol / 3 h / 20 °C 13.1: potassium carbonate / acetone / 5 h / 20 °C 14.1: dichloromethane / 0.5 h / 20 °C 15.1: lithium hydroxide hydrate / water; tetrahydrofuran / 1 h / 20 °C 16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / |Inert atmosphere View Scheme

ammonium phosphate monobasic; D-glucose; phosphate buffer pH 6.3; magnesium sulfate in dimethyl sulfoxide other reducing agents, other substrates; MechanismProduct distribution;