1: sodium hydride / mineral oil; tetrahydrofuran / 16.33 h / |Inert atmosphere; |Reflux 2: tert.-butylnitrite; anhydrous iron chloride / 12 h / 30 °C View Scheme

tetrachlorosilane in ethanol T=20°C;

lithium hexamethyldisilazane; Verkade nonionic superbase; palladium diacetate in tetrahydrofuran; toluene T=80°C; 32 h;

1: 98 percent / TsOH / benzene / 20 h / Heating 2: 1.) Mg, I2 / 1.) anhydrous THF, 4 h, 60 deg C, 2.) THF 3: 97 percent / H2O, 10percent HCl / methanol / 1 h / Ambient temperature 4: 1.) t-BuOK / 1.) anhydrous THF, 30 min, RT, 2.) THF, RT, 24 h 5: 58 percent / LAH / diethyl ether / 6 h / -78 °C 6: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 7: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 8: 98 percent / ICl / CH2Cl2 / Ambient temperature 9: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 10: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: sodium hydride / mineral oil; toluene / 7 h / 20 - 110 °C / |Inert atmosphere 2: sodium tetrahydroborate / methanol / 10 °C View Scheme

hydrogenchloride in ethanol; water Mannich Reaction; Heating / reflux;

potassium phosphate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water T=80°C; 5 h; Sealed tubeInert atmosphere;

potassium permanganate; NaOD; copper aluminide 1.) addition gradually, 50 deg C, 140 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;