1: 1.) 3-chloroperoxybenzoic acid, 2.) NaOH / 1.) CHCl3, room temperature, 20 min, 2.) reflux, 1.5 h 2: 73 percent / H2 / Pd-C / ethyl acetate / 2 h / 760 Torr / Ambient temperature 3: 1.) BuLi / 1.) THF, -105 deg C -> room temperature, 1,5 h 4: 84 percent / W-2 Raney nickel / ethanol / 1 h / Ambient temperature View Scheme

1: 1.) 3-chloroperoxybenzoic acid, 2.) NaOH / 1.) CHCl3, room temperature, 20 min, 2.) reflux, 1.5 h 2: 73 percent / H2 / Pd-C / ethyl acetate / 2 h / 760 Torr / Ambient temperature 3: 80 percent / -105 deg C -> room temperature, 1.5 h 4: 84 percent / W-2 Raney nickel / ethanol / 1 h / Ambient temperature View Scheme

1: 1.) 3-chloroperoxybenzoic acid, 2.) NaOH / 1.) CHCl3, room temperature, 20 min, 2.) reflux, 1.5 h 2: 73 percent / H2 / Pd-C / ethyl acetate / 2 h / 760 Torr / Ambient temperature 3: 68 percent / n-BuLi / tetrahydrofuran / -105 deg C -> room temperature, 1.5 h 4: W-2 Raney nickel / ethanol / 1 h / Ambient temperature View Scheme

1: With tert.-butyl lithium in diethyl ether; pentane T=-78°C; 1 h; 2: With indium(III) chloride in tetrahydrofuran; diethyl ether; pentane T=-78°C; 1 h; 3: With water in tetrahydrofuran; diethyl ether; pentane Heating; Further stages.;

1: With tert.-butyl lithium in diethyl ether; pentane T=-78°C; 1 h; 2: With indium(III) chloride in tetrahydrofuran; diethyl ether; pentane T=-78°C; 1 h; 3: in tetrahydrofuran; diethyl ether; pentane T=20°C; 18 h; Irradiation; Further stages.;

1: 1.) 3-chloroperoxybenzoic acid, 2.) NaOH / 1.) CHCl3, room temperature, 20 min, 2.) reflux, 1.5 h 2: 73 percent / H2 / Pd-C / ethyl acetate / 2 h / 760 Torr / Ambient temperature 3: 78 percent / n-BuLi / tetrahydrofuran / -105 deg C -> room temperature, 1.5 h 4: 86 percent / W-2 Raney nickel / ethanol / 1 h / Ambient temperature View Scheme