1: 1.) NaH, 2.) benzyl bromide / 1.) THF, toluene, -20 deg C, 1 h, 2.) THF, toluene, -20 deg C, 2 h 2: DBU / toluene; tetrahydrofuran / 2 h 3: 89 percent / phosphate buffer pH 3 / 2.5 h / Ambient temperature View Scheme

Multi-step reaction with 8 steps 1: 90 percent / K2CO3 / acetone / 4 h / Heating2: 100 percent / NaH / tetrahydrofuran / 2 h / 0 °C3: 100 percent / H2 / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature4: Et3N / CH2Cl2 / 1 h5: CH2Cl2 / 1 h6: 86 percent / anisole, TiCl4 / CH2Cl2 / 1 h / 0 °C7: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C8: 98 percent / Et3N / toluene / 5 h / Ambient temperature  

Multi-step reaction with 5 steps 1: Et3N / CH2Cl2 / 1 h2: CH2Cl2 / 1 h3: 86 percent / anisole, TiCl4 / CH2Cl2 / 1 h / 0 °C4: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C5: 98 percent / Et3N / toluene / 5 h / Ambient temperature  

Multi-step reaction with 3 steps 1: 86 percent / anisole, TiCl4 / CH2Cl2 / 1 h / 0 °C2: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C3: 98 percent / Et3N / toluene / 5 h / Ambient temperature