1: 78.6 percent / AgNO3, 8percent KOH / ethanol; H2O / 2 h / 0 °C 2: 1) O3, 2) Me2S / 1) CH2Cl2, -78 degC, 2) room temp., 1 h 3: oxalyl chloride, pyridine / benzene / 6 h / Ambient temperature 4: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 5: 90.5 percent / ZnCl2, K / tetrahydrofuran / 1) room temp., 1 h, 2) 40-50 degC, 1 h 6: 10 percent / tetrahydrofuran / 1) -78 degC, 2) -20 degC, 30 min View Scheme

potassium hydroxide; silver nitrate in ethanol; water T=0°C; 2 h;

1: 78.6 percent / AgNO3, 8percent KOH / ethanol; H2O / 2 h / 0 °C 2: 1) O3, 2) Me2S / 1) CH2Cl2, -78 degC, 2) room temp., 1 h View Scheme

1: LiAlH4 / diethyl ether / 1.) -78 deg C, 35 min 2.) 0 deg C, 1 h 2: 76 percent / 48percent HBr / pentane / 0.67 h / 0 °C View Scheme

1: 85 percent / NaBH4 / diethyl ether; methanol / 12 h / 0 deg C to RT 2: 3.5 g / Hg(OAc)2 / propionic acid / 5 h / 220 °C 3: 1.) O3, 2.) Zn/AcOH / 1.) CH2Cl2, -78 deg C, 2h, 2.) RT, 2h View Scheme