potassium carbonate in N,N-dimethyl-formamide T=20°C;

hydrogen; palladium dihydroxide in methanol P=3620.04 Torr; 120 h;

sodium hydrogencarbonate in water T=20°C;

triethylamine in N,N-dimethyl-formamide 8 h; Ambient temperature;

tetrabutyl ammonium fluoride in tetrahydrofuran 0.166667 h;

magnesium 1 h; sonication: 35 kHz, 120-240 W;

1: Et3N / acetonitrile; H2O / 1 h / 0 °C 2: 95 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C 3: 75 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C 4: diethyl ether View Scheme

1: 95 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C 2: 75 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C 3: diethyl ether View Scheme

1: 1) n-BuLi, 2) KH / 1) THF, hexane, -78 deg C, 30 min, 2) a) to r.t., 1 h, b) -78 deg C to r.t., 140 min, c) 45-50 deg C, 17 h 2: 1) LDA / 1) THF, hexane, -78 deg C, 6 min, 2) THF, a) -78 deg C, 105 min, b) to r.t., 105 min 3: 100 percent / Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C 4: 94 percent / n-Bu4NF / tetrahydrofuran / 0.17 h View Scheme

1: 1) LDA / 1) THF, hexane, -78 deg C, 6 min, 2) THF, a) -78 deg C, 105 min, b) to r.t., 105 min 2: 100 percent / Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C 3: 94 percent / n-Bu4NF / tetrahydrofuran / 0.17 h View Scheme