1: With n-butyllithium in diethyl ether; hexane T=0 - 20°C; 3.25 h; 2: With iodine in diethyl ether; hexane T=0 - 20°C; 2.5 h;

diisobutylaluminium hydride in hexane; toluene T=-78 - 20°C; Inert atmosphere;

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 1.2: 8 h / -78 - 20 °C / Inert atmosphere 2.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere View Scheme

1.1: tetrahydrofuran / Inert atmosphere 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 2.2: 8 h / -78 - 20 °C / Inert atmosphere 3.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere 4.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / Inert atmosphere 2.1: tetrahydrofuran / Inert atmosphere 3.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 3.2: 8 h / -78 - 20 °C / Inert atmosphere 4.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / hexane; toluene / -78 - 20 °C / Inert atmosphere View Scheme

1.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / |Inert atmosphere 1.2: 1 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / 4 h / 0 - 20 °C / |Inert atmosphere 2.2: 0.5 h / 0 - 20 °C / |Inert atmosphere 2.3: 0 °C View Scheme

1.1: Jone's reagent / acetone / 0.17 h / 0 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere 2.2: Inert atmosphere; Cooling View Scheme