tin; cyclohexene in methanol; acetic acid 1.)room temperature, 2 h, 2.)electrolysis, 50-55 deg C;

tin(ll) chloride; palladium in various solvent(s) T=25°C; 85 h;

titanium tetrachloride in dichloromethane

1: 1. NaH 2. <Bu4N>I / 1. THF, room temperature, 1.5 h 2. 2 h, room temperature, then 2 h, reflux 2: 97 percent / LiAlH4 / tetrahydrofuran 3: 1. BH3 2. NaOH, H2O2 / 1. THF, 15 min, room temperature 2. 1.5 h, H2O, MeOH, room temperature 4: H2 / Pd-C / ethanol / 48 h / Ambient temperature View Scheme

1: 1. NaH 2. <Bu4N>I / 1. THF, room temperature, 1.5 h 2. 2 h, room temperature, then 2 h, reflux 2: 97 percent / LiAlH4 / tetrahydrofuran 3: 1. BH3 2. NaOH, H2O2 / 1. THF, 15 min, room temperature 2. 1.5 h, H2O, MeOH, room temperature 4: H2 / Pd-C / ethanol / 48 h / Ambient temperature 5: 911 mg / p-TosOH / acetone / 5 h / Ambient temperature View Scheme