hydrogen; 5 percent palladium-carbon; palladium dichloride in ethanol; ethyl acetate P=750.06 Torr;

1.1: 96 percent / H2 / Pd on CaCO3 / tetrahydrofuran / 1500.12 Torr 2.1: LiHMDS / -78 °C 2.2: MoOPH / 0.5 h / -25 °C 3.1: 85 percent / pyridine / 0 - 20 °C 4.1: tetrahydrofuran; toluene; pyridine / -40 °C 5.1: H2 / Pd on CaCO3 / tetrahydrofuran / 1500.12 Torr 6.1: K2CO3 / methanol 7.1: DEAD; PPh3 / tetrahydrofuran / 0 °C 8.1: aq. K2CO3 / methanol 9.1: 70 percent / NaOAc / 60 °C 10.1: FeCl3*6H2O / CH2Cl2 / 0.33 h / 20 °C 11.1: pyridine / -20 °C 12.1: NaI / butan-2-one / 80 °C 13.1: 72 percent / aq. K2CO3 / methanol 14.1: 92 percent / ethanol / Heating View Scheme

hydrogenchloride in methanol 2 h; Ambient temperature;

hydrogen; Lindlar's catalyst in tetrahydrofuran Catalytic hydrogenation; P=1500.12 Torr;

pyridine T=70°C; tritylation; 16 h;

18-crown-6 ether in water; ethyl acetate T=50°C; 14 h;

1: acetone / 2 h / Heating 2: W-2 Raney Ni / tetrahydrofuran / 3 h / Heating View Scheme

1: 84 percent / pyridine / 16 h / 70 °C 2: 79 percent / acetone / 3.5 h / Heating 3: 1.) Ni(Ra), acetone / 1.) reflux, overnight, 2.) THF, reflux, 24 h View Scheme

1: lithium diisopropylamide (LDA) / tetrahydrofuran / -78 °C 2: NaIO4, 18-crown-6 / H2O; ethyl acetate / 60 °C View Scheme

1: 84 percent / pyridine / 16 h / 70 °C 2: 79 percent / acetone / 3.5 h / Heating 3: 1.) Ni(Ra), acetone / 1.) reflux, overnight, 2.) THF, reflux, 24 h View Scheme