palladium on activated charcoal T=260°C;

lithium aluminium tetrahydride in tetrahydrofuran Reflux;

1: With acetic acid in ethanol 0.5 h; Reflux; 2: With sodium cyanoborohydride in ethanol 1.5 h; Reflux; 3: With ammonia in water

1: With diisobutylaluminium hydride in tetrahydrofuran; hexane; dichloromethane T=0 - 20°C; 1 h; Inert atmosphere; 2: With water; NAF in tetrahydrofuran; hexane; dichloromethane T=0°C; 0.5 h; Inert atmosphere; regioselective reaction;

diisobutylaluminium hydride; [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in toluene T=20°C; 2 h;

hydrogenchloride in water; acetonitrile T=170°C; Diels-Alder Cycloaddition; 5 h; Inert atmosphereMicrowave irradiation;

1.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 1.2: 74 percent / hexane; tetrahydrofuran / 5.25 h 2.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 2.2: 71 percent / H2O / tetrahydrofuran; pentane / 3 h / 20 °C 3.1: 0.25 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 1.2: 80 percent / hexane; tetrahydrofuran / 5.25 h 2.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 2.2: 75 percent / hexane; tetrahydrofuran / 5.25 h 3.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 3.2: 74 percent / hexane; tetrahydrofuran / 5.25 h 4.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 4.2: 71 percent / H2O / tetrahydrofuran; pentane / 3 h / 20 °C 5.1: 0.25 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 1.2: 75 percent / hexane; tetrahydrofuran / 5.25 h 2.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 2.2: 74 percent / hexane; tetrahydrofuran / 5.25 h 3.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 3.2: 71 percent / H2O / tetrahydrofuran; pentane / 3 h / 20 °C 4.1: 0.25 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 1.2: 71 percent / H2O / tetrahydrofuran; pentane / 3 h / 20 °C 2.1: 0.25 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme