10 Pd-BaSO4; hydrogen in toluene Rosenmund reduction; P=760.051 Torr; 3 h; Reflux;

triethylsilane; 10 palladium on carbon in acetone

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 1.2: 1.5 h / 20 °C / |Inert atmosphere 2.1: triethylsilane; 5 palladium on charcoal / tetrahydrofuran / 7 h / |Inert atmosphere View Scheme

lithium diisopropyl amide in tetrahydrofuran T=-70°C; 0.5 h; Yield given. Yields of byproduct given;

titanium tetrachloride in diethyl ether; Petroleum ether 1.) 20 deg C, 5 min, 2.) -45 deg C, 5 min; Yield given. Yields of byproduct given;

titanium tetrachloride in dichloromethane 1.) 20 deg C, 5 min, 2.) -45 deg C, 5 min; Yield given. Yields of byproduct given;

1: (3S)-3,5-dimethylhepta-4,6-dien-2-one With lithium diisopropyl amide in tetrahydrofuran T=-70°C; enolation; 0.0833333 h; 2: 4-(2-0xoethyl)-2,6-piperidinedione in tetrahydrofuran aldolisation; 0.5 h;