1.1: hydrogen / platinum(IV) oxide / ethyl acetate / 14 - 16 h / 3620.13 Torr 2.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 3.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 4.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 5.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 5.2: 0 - 5 °C 6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 6.2: pH 1 - 2 View Scheme

Multi-step reaction with 5 steps 1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere3.3: Cooling4.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere5.1: ethylaluminum dichloride / dichloromethane; toluene / 0.25 h / 0 °C / Inert atmosphere5.2: 18.33 h / 0 - 25 °C / Inert atmosphere5.3: 0 °C  

Multi-step reaction with 4 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere2.3: Cooling3.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere4.1: ethylaluminum dichloride / dichloromethane; toluene / 0.25 h / 0 °C / Inert atmosphere4.2: 18.33 h / 0 - 25 °C / Inert atmosphere4.3: 0 °C  

Multi-step reaction with 2 steps 1.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere2.1: ethylaluminum dichloride / dichloromethane; toluene / 0.25 h / 0 °C / Inert atmosphere2.2: 18.33 h / 0 - 25 °C / Inert atmosphere2.3: 0 °C