ethyl magnesium chloride; iron(II) chloride in tetrahydrofuran; m-xylene T=20°C; 1 h;

diisobutylaluminium hydride in hexane; dichloromethane T=20°C; Reduction; Claisen rearrangement; 12 h;

ytterbium(III) triflate in acetonitrile Substitution; Claisen rearrangement; 48 h; Heating;

1.1: 76 percent / 6 h / 210 °C 2.1: 84 percent / imidazole / CH2Cl2 / 10 h / 20 °C 3.1: BH3*DMS / tetrahydrofuran / 1.5 h / 10 °C 3.2: 75 percent / 30 percent H2O2 / 2 h / 0 °C 4.1: Dess-Martin periodinane; PhCO2H / CH2Cl2; dimethylsulfoxide / 0.5 h 5.1: 4.4 g / CH2Cl2; dimethylsulfoxide / 10 h / 20 °C 6.1: 78 percent / DIBAL-H / CH2Cl2; hexane / 0 - 20 °C 7.1: 80 percent / TBAF / tetrahydrofuran / 3 h / 20 °C 8.1: 65 percent / (+)-DET; Ti(OPr-i)4; TBHP / 4 h / -20 °C 9.1: 82 percent / pyridine / CH2Cl2 / 10 h / 20 °C View Scheme

1.1: 76 percent / 6 h / 210 °C 2.1: 84 percent / imidazole / CH2Cl2 / 10 h / 20 °C 3.1: BH3*DMS / tetrahydrofuran / 1.5 h / 10 °C 3.2: 75 percent / 30 percent H2O2 / 2 h / 0 °C 4.1: Dess-Martin periodinane; PhCO2H / CH2Cl2; dimethylsulfoxide / 0.5 h 5.1: 4.4 g / CH2Cl2; dimethylsulfoxide / 10 h / 20 °C 6.1: 78 percent / DIBAL-H / CH2Cl2; hexane / 0 - 20 °C 7.1: 80 percent / TBAF / tetrahydrofuran / 3 h / 20 °C 8.1: 65 percent / (+)-DET; Ti(OPr-i)4; TBHP / 4 h / -20 °C View Scheme

1.1: 76 percent / 6 h / 210 °C 2.1: 84 percent / imidazole / CH2Cl2 / 10 h / 20 °C 3.1: BH3*DMS / tetrahydrofuran / 1.5 h / 10 °C 3.2: 75 percent / 30 percent H2O2 / 2 h / 0 °C 4.1: Dess-Martin periodinane; PhCO2H / CH2Cl2; dimethylsulfoxide / 0.5 h 5.1: 4.4 g / CH2Cl2; dimethylsulfoxide / 10 h / 20 °C 6.1: 78 percent / DIBAL-H / CH2Cl2; hexane / 0 - 20 °C 7.1: 80 percent / TBAF / tetrahydrofuran / 3 h / 20 °C 8.1: 65 percent / (-)-DET; Ti(OPr-i)4; TBHP / 4 h / -20 °C 9.1: 61 percent / DEAD; TPP / tetrahydrofuran / -20 - 20 °C 10.1: 72 percent / NaOMe / methanol / 3 h / 20 °C 11.1: 75 percent / pyridine / CH2Cl2 / 10 h / 20 °C View Scheme

3-chloro-benzenecarboperoxoic acid in chloroform T=0°C;