1: 2.) HCl / 1.) Et2O 2: NaBH4 / ethanol 3: 96 percent / NaOMe / methanol View Scheme

1: CH2Cl2 / 3 h / Ambient temperature 2: LAH / tetrahydrofuran / 1 h / 0 - 25 °C 3: VCl3(THF)3, Zn-Cu / CH2Cl2 / 3 h / Ambient temperature 4: N,N-diisopropylethylamine / dimethylformamide / 18 h / Ambient temperature 5: cyclohexene / 20percent Pd(OH)2/C / ethanol / 18 h / Heating 6: CH2Cl2 / 18 h / Heating 7: NaH / dimethylformamide / 18 h / Ambient temperature 8: 4 N HCl / methanol; dioxane / 18 h / Ambient temperature View Scheme

1: diethyl ether / a) 0 deg C, 2 h, b) RT, overnight 2: HCl / dioxane; diethyl ether / 1 h / 0 °C View Scheme

hydrogenchloride 1.) Et2O; Yield givenMultistep reaction;

tetra(n-butyl)ammonium hydroxide in water; dimethyl sulfoxide T=0°C; 0.5 h;

1: diethyl ether / 0.17 h / Ambient temperature 2: 63 percent / silver benzoate, Et3N / 0.5 h / Ambient temperature 3: 93 percent / H2 / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature View Scheme

1: CH2Cl2 / 3 h / Ambient temperature 2: LAH / tetrahydrofuran / 1 h / 0 - 25 °C 3: VCl3(THF)3, Zn-Cu / CH2Cl2 / 3 h / Ambient temperature 4: N,N-diisopropylethylamine / dimethylformamide / 18 h / Ambient temperature 5: cyclohexene / 20percent Pd(OH)2/C / ethanol / 18 h / Heating 6: CH2Cl2 / 18 h / Heating 7: NaH / dimethylformamide / 18 h / Ambient temperature 8: 4 N HCl / methanol; dioxane / 18 h / Ambient temperature View Scheme

1: CH2Cl2 / 3 h / Ambient temperature 2: LAH / tetrahydrofuran / 1 h / 0 - 25 °C 3: VCl3(THF)3, Zn-Cu / CH2Cl2 / 3 h / Ambient temperature 4: N,N-diisopropylethylamine / dimethylformamide / 18 h / Ambient temperature 5: cyclohexene / 20percent Pd(OH)2/C / ethanol / 18 h / Heating 6: CH2Cl2 / 18 h / Heating 7: NaH / dimethylformamide / 18 h / Ambient temperature 8: 4 N HCl / methanol; dioxane / 18 h / Ambient temperature View Scheme

1: CH2Cl2 / 0 - 20 °C 2: aq. LiOH / tetrahydrofuran / 0 - 22 °C View Scheme