potassium hydroxide in tetrahydrofuran; water T=20°C;

sodium hypophosphite; 2-methyl propanoic acid; palladium on activated charcoal in 1,4-dioxane; water T=20°C; 48 h;

camphor-10-sulfonic acid 12 h; Ambient temperature;

1: tetrahydrofuran / 2 h / 0 °C 2: triethylamine / tetrahydrofuran / 4 h / 20 °C 3: 74 percent / NaH2PO2*H2O / palladium on activated charcoal / dioxane; H2O / 48 h / 20 °C View Scheme

1: triethylamine / tetrahydrofuran / 4 h / 20 °C 2: 74 percent / NaH2PO2*H2O / palladium on activated charcoal / dioxane; H2O / 48 h / 20 °C View Scheme

1: KOH / ethanol; H2O / 10 h / Heating 2: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme

1: Zn, NH4Cl / ethanol; H2O 2: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 3: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 4: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 5: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 6: ethanol / 2 h / Heating 7: KOH / ethanol; H2O / 10 h / Heating 8: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme

1: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 2: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 3: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 4: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 5: ethanol / 2 h / Heating 6: KOH / ethanol; H2O / 10 h / Heating 7: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme

1: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 2: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 3: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 4: ethanol / 2 h / Heating 5: KOH / ethanol; H2O / 10 h / Heating 6: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme

1: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 2: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 3: ethanol / 2 h / Heating 4: KOH / ethanol; H2O / 10 h / Heating 5: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme