1.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C 1.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating 2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C 2.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C 2.3: tetrahydrofuran; hexane / -85 - -20 °C 3.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr 4.1: 93 percent / 0.6 N aq. NaOH / 20 h / 4 °C 5.1: 79 percent / triethylamine; isopropenyl chloroformate / tetrahydrofuran / 1.25 h / 0 - 20 °C View Scheme

1.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C 1.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating 2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C 2.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C 2.3: tetrahydrofuran; hexane / -85 - -20 °C 3.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr 4.1: 93 percent / 0.6 N aq. NaOH / 20 h / 4 °C View Scheme