1: With sulfuric acid; sodium nitrite in water T=0°C; 0.5 h; 2: With urea in water T=0°C; 0.5 h; 3: With potassium iodide in water T=20°C; 1 h;

boron trifluoride diethyl etherate in dichloromethane; acetonitrile T=-50°C; 2 h; Inert atmosphere;

1.1: 75 percent / Ph3P; iPr2NEt / Pd(OAc)2 / dimethylformamide / 80 °C 2.1: O3 / CH2Cl2; methanol / -78 °C 2.2: 63 percent / NaBH4 / 20 °C 3.1: PPL / diethyl ether / 39 °C 4.1: Et3N; 4-DMAP / CH2Cl2 / 20 °C 4.2: 65 percent / NaBH4 / dimethylsulfoxide / 60 °C 5.1: 84 percent / nBu3P / pyridine / 20 °C 6.1: 100 percent / MCPBA; KHCO3 / CH2Cl2 / 20 °C 7.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / -78 °C 8.1: 83 percent / Na-Hg; Na2HPO4 / methanol / 20 °C 9.1: 78 percent / L-Selectride / tetrahydrofuran / Heating View Scheme