hydrogen; Pa/C in ethanol P=760 Torr; Ambient temperature;

1: 77 percent / dimethylsulfoxide / 3 h / 125 °C 2: 1.) 5percent CuI, methyl sulfide / 1.) THF, -23 deg C, 10 min 2.) -23 deg C, 15 min, room temp. 3: o-Chloranil / toluene / 15 h / Ambient temperature 4: 91 percent / H2 / 10percent Pa/C / ethanol / 760 Torr / Ambient temperature View Scheme

1: 1.) 5percent CuI, methyl sulfide / 1.) THF, -23 deg C, 10 min 2.) -23 deg C, 15 min, room temp. 2: o-Chloranil / toluene / 15 h / Ambient temperature 3: 91 percent / H2 / 10percent Pa/C / ethanol / 760 Torr / Ambient temperature View Scheme

1: o-Chloranil / toluene / 15 h / Ambient temperature 2: 91 percent / H2 / 10percent Pa/C / ethanol / 760 Torr / Ambient temperature View Scheme

ammonia; sodium in diethyl ether Birch reduction; 0.5 h;

hydrogen iodide 16 h; Heating;

Pseudomonas putida UV4; oxygen Enzymatic reaction;