1: pyridine; diethyl ether / 6 h / Heating 2: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 3: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 4: 77 percent / H2SO4 conc. / 4 h / Heating 5: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 6: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 7: diethyl ether / 0.5 h / 0 °C 8: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

oxalyl dichloride; dimethyl sulfoxide; triethylamine Yield given. Multistep reaction;

1: dimethylsulfide; ozone / dichloromethane / -78 °C 2: pyridine; palladium diacetate / toluene / 80 °C / Molecular sieve View Scheme

sodium tetrahydroborate; diammonium oxalate in acetonitrile T=20°C; 0.166667 h;

1: With Co(3-Me-5-MeO-salen) in acetonitrile T=-20 - 20°C; 0.166667 h; Inert atmosphere; 2: With dihydrogen peroxide in water; acetonitrile T=-20°C; 24 h; Inert atmosphere; Further stages;

hydrogen in water T=29.84°C; P=6000.6 Torr; 6 h; AutoclaveSealed tube; chemoselective reaction;

Kaolinitic clay; water 0.025 h; Irradiationmicrowave;

1: 1.) OsO4, NMO, H2O, 2.) NaIO4, H2O / 1.) acetone, 2.) THF 3: Na, liq. NH3 View Scheme

2: Na, liq. NH3 View Scheme

1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min 2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C View Scheme