1: 95 percent / KOH, CaCl2, NaBH4 / ethanol; H2O / 5 h / Ambient temperature 2: 1.) LDA / 1.) THF, 2 h, -78 deg C; 2.) THF + HMPT, -78 deg C, 2 h 3: 57 percent / Pd/C, H2 / ethyl acetate; acetic acid / 16 h / 2250.2 Torr / Ambient temperature View Scheme

potassium hydroxide; sodium tetrahydroborate; calcium chloride in ethanol

Multi-step reaction with 2 steps 1: sodium methoxide2: 80 percent / H2, NEt3 / <Rh(1,5-cyclooctadiene)Cl>2, (4S,5S)-MOD-DIOP (12) / methanol / 40 h / 30 °C / 760 Torr