1: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h 2: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT 3: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h 4: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C 5: LiAlH4 / diethyl ether / 1 h / 0 °C 7: (n-Bu)3SnH / toluene / 3 h / Heating 8: 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

Multi-step reaction with 3 steps 1: pyridine / diethyl ether / 0.5 h / 0 °C2: 0.67 h / 100 - 110 °C3: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C  

Multi-step reaction with 4 steps 1: HgO, BF3-etherate / tetrahydrofuran; H2O / 0.75 h / Ambient temperature2: pyridine / diethyl ether / 0.5 h / 0 °C3: 0.67 h / 100 - 110 °C4: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C  

Multi-step reaction with 2 steps 1: 0.67 h / 100 - 110 °C2: sodium hydride / tetrahydrofuran; paraffin / 0.17 h / 0 - 25 °C  

With  hydrogen; sodium hydrogencarbonate; palladium on activated charcoal in  1,4-dioxane 3 h;   

Multi-step reaction with 2 steps 1: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h2: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT  

Multi-step reaction with 3 steps 1: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h2: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT3: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h  

Multi-step reaction with 4 steps 1: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h2: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT3: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h4: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C  

Multi-step reaction with 5 steps 1: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h2: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT3: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h4: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C5: LiAlH4 / diethyl ether / 1 h / 0 °C  

Multi-step reaction with 6 steps 1: 99 percent / H2, NaHCO3 / 10 percent Pd-C / dioxane / 3 h2: 1.) LDA / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C to RT3: 1.) zinc acetate; 2.) 5 percent KOH / 1.) acetic acid, reflux, 1 h; 2.) MeOH, reflux, 0.5 h4: N,N-diethylcyclohexylamine / dioxane / 2 h / 60 °C5: LiAlH4 / diethyl ether / 1 h / 0 °C