diisobutylaluminium hydride in tetrahydrofuran T=-78°C; 0.5 h;

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 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 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 View Scheme

1: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 2: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: ethanol / 2 h / Heating 2: KOH / ethanol; H2O / 10 h / Heating View Scheme

in ethanol 2 h; Heating; Yield given;

1: ethanol / 2 h / Heating 2: KOH / ethanol; H2O / 10 h / Heating 3: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme