water; ozone ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux; Yield given. Multistep reaction;

1: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux 2: 90 percent / NaOH, AgNO3 / ethanol; H2O / 4 h View Scheme

palladium-barium carbonate; ethanol Hydrogenation;

1.1: 96 percent / piperidine / benzene / 4 h / Heating 2.1: 85 percent / DIBAL-H / toluene / 2 h 3.1: MeOK / 48 h / 20 °C 4.1: piperidine / 4 h / Heating 4.2: DIBAL-H / toluene / 2 h 5.1: 85 percent / LiAlH4; TiCl3 / tetrahydrofuran View Scheme