1: 98 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 30 min 2: 85 percent / MCPBA / CH2Cl2 / 2 h / Ambient temperature 3: 95 percent / DMAP, Et3N / CH2Cl2 / 1) 0 deg C 1 h, 2) r.t., 1 h 4: 50 percent / LDA, n-BuLi, HMPT / tetrahydrofuran; hexane / 1) -20 deg C, 10 min, 2) 20 deg C, 2+20 h 5: 42 percent / Na/Hg / methanol / 48 h / 25 °C 6: 65 percent / CsF / tetrahydrofuran / 3 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 1) 0 deg C, 1 h, 2) r.t., 30 min;

Multi-step reaction with 5 steps 1: 98 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 30 min2: 85 percent / MCPBA / CH2Cl2 / 2 h / Ambient temperature3: 95 percent / DMAP, Et3N / CH2Cl2 / 1) 0 deg C 1 h, 2) r.t., 1 h4: 50 percent / LDA, n-BuLi, HMPT / tetrahydrofuran; hexane / 1) -20 deg C, 10 min, 2) 20 deg C, 2+20 h5: 42 percent / Na/Hg / methanol / 48 h / 25 °C  

Multi-step reaction with 3 steps 1: 98 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 30 min2: 85 percent / MCPBA / CH2Cl2 / 2 h / Ambient temperature3: 95 percent / DMAP, Et3N / CH2Cl2 / 1) 0 deg C 1 h, 2) r.t., 1 h  

Multi-step reaction with 4 steps 1: 98 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 30 min2: 85 percent / MCPBA / CH2Cl2 / 2 h / Ambient temperature3: 95 percent / DMAP, Et3N / CH2Cl2 / 1) 0 deg C 1 h, 2) r.t., 1 h4: 50 percent / LDA, n-BuLi, HMPT / tetrahydrofuran; hexane / 1) -20 deg C, 10 min, 2) 20 deg C, 2+20 h  

Multi-step reaction with 4 steps 1: 98 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 30 min2: 85 percent / MCPBA / CH2Cl2 / 2 h / Ambient temperature3: 95 percent / DMAP, Et3N / CH2Cl2 / 1) 0 deg C 1 h, 2) r.t., 1 h4: 20 percent / n-BuLi / tetrahydrofuran / 1) -78 deg C, 0.5+0.5 h, 2) r.t., 1 h  

Multi-step reaction with 5 steps 1: 98 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 30 min2: 85 percent / MCPBA / CH2Cl2 / 2 h / Ambient temperature3: 95 percent / DMAP, Et3N / CH2Cl2 / 1) 0 deg C 1 h, 2) r.t., 1 h4: 20 percent / n-BuLi / tetrahydrofuran / 1) -78 deg C, 0.5+0.5 h, 2) r.t., 1 h5: 85 percent / NEt3 / CH2Cl2 / 1 h / 0 °C