ammonium acetate in ethanol 3 h; Heating;

in chloroform T=20 - 60°C; Diels-Alder reaction; 14 h; regioselective reaction;

nickel T=160°C; P=15200 Torr; Hydrogenation;

1: hydrogenchloride / methanol; dichloromethane / 1 h / 40 °C 2: sodium hydroxide; hydroxylamine-o-sulphonic acid / ethanol; water / 0.5 h / 60 °C 3: sodium periodate / dichloromethane; water / 12 h / 0 °C 4: chloroform / 14 h / 20 - 60 °C View Scheme

1: sodium hydroxide; hydroxylamine-o-sulphonic acid / ethanol; water / 0.5 h / 60 °C 2: sodium periodate / dichloromethane; water / 12 h / 0 °C 3: chloroform / 14 h / 20 - 60 °C View Scheme

1: sodium periodate / dichloromethane; water / 12 h / 0 °C 2: chloroform / 14 h / 20 - 60 °C View Scheme

ammonia; sodium hydride 1.) diethylene glycol, 40 deg C, 3 h, 2.) 160 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;