5 Pd(OH)2/C; hydrogen in tetrahydrofuran; methanol; water T=20°C; 0.5 h;

1.1: DDQ / CH2Cl2 / 3 h / 20 °C 1.2: 63 percent / DMAP / CH2Cl2 / 0.33 h 2.1: 99 percent / N-bromosuccinimide / CH2Cl2 / -78 - 20 °C 3.1: 43 percent / TiCl4 / CH2Cl2; tetrahydrofuran / 3 h / 20 °C 4.1: 99 percent / H2; Et3N; NaHCO3 / Pd(OH)2/C / H2O; methanol; ethyl acetate / 18 h / 20 °C View Scheme

1: 80 percent / DMAP / CH2Cl2 / 20 °C 2: 80 percent / H2 / Pd(OH)2/C / methanol; tetrahydrofuran / 6 h / 20 °C View Scheme

1.1: DDQ / CH2Cl2 / 3 h / 20 °C 1.2: 63 percent / DMAP / CH2Cl2 / 0.33 h 2.1: 99 percent / N-bromosuccinimide / CH2Cl2 / -78 - 20 °C 3.1: 47 percent / TiCl4 / CH2Cl2; tetrahydrofuran / 3 h / 20 °C 4.1: 100 percent / H2; Et3N; NaHCO3 / Pd(OH)2/C / H2O; methanol; ethyl acetate / 18 h / 20 °C View Scheme

1: 53 percent / TiCl4 / CH2Cl2; tetrahydrofuran / 5 h / 20 °C 2: 100 percent / H2; Et3N; NaHCO3 / Pd(OH)2/C / H2O; methanol; ethyl acetate / 18 h / 20 °C View Scheme

Multi-step reaction with 3 steps 1.1: 52 percent / DDQ / CH2Cl2 / 20 °C2.1: 53 percent / TiCl4 / CH2Cl2; tetrahydrofuran / 20 °C3.1: tri-O-benzylgallic acid chloride; pyridine; DMAP / 20 °C3.2: 90 percent / H2 / 20 percent Pd(OH)2/C / tetrahydrofuran; methanol; H2O / 750.06 Torr