1: 100 percent / hydrogen / platinum oxide / acetic acid / 24 h 2: 74 percent / 1M-barium hydroxide / H2O / 1 h / Heating View Scheme

1: 100 percent / hydrogen / platinum oxide / acetic acid / 24 h 2: 76 percent / liquid ammonia, sodium / methanol View Scheme

1: 57 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 96 h / Ambient temperature 2: hydrogen / platinum oxide / acetic acid 3: 1.) 1M-diborane, 2.) barium hydroxide / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 1 h, 3.) water, RT, 12 h View Scheme