hydrogen; palladium on activated charcoal in methanol 48 h; Ambient temperature;

benzeneseleninic acid; dihydrogen peroxide in dichloromethane 60 h; Ambient temperature;

1: 68 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature 2: 86 percent / pyridine / 5 h / Ambient temperature 3: 77 percent / MeSO2Cl, Et3N / diethyl ether / a) 0 deg C, 5 h, b) RT, overnight 4: 75 percent / 20 percent KOH / ethanol / 1 h / Ambient temperature 5: 100 percent / H2 / 5 percent Pd/C / methanol / 48 h / Ambient temperature View Scheme

1: 65 percent / m-CPBA / CHCl3 / Ambient temperature 2: 68 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature 3: 86 percent / pyridine / 5 h / Ambient temperature 4: 77 percent / MeSO2Cl, Et3N / diethyl ether / a) 0 deg C, 5 h, b) RT, overnight 5: 75 percent / 20 percent KOH / ethanol / 1 h / Ambient temperature 6: 100 percent / H2 / 5 percent Pd/C / methanol / 48 h / Ambient temperature View Scheme

1: 66 percent / zinc bromide / CH2Cl2 / 48 h / Ambient temperature 2: 97 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / 0 °C 3: 97 percent / benzeneselenic acid, 30percent hydrogen peroxide / CH2Cl2 / 60 h / Ambient temperature View Scheme

1: 97 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / 0 °C 2: 97 percent / benzeneselenic acid, 30percent hydrogen peroxide / CH2Cl2 / 60 h / Ambient temperature View Scheme