pyridinium chlorochromate in dichloromethane 1.5 h;

diisobutylaluminium hydride in diethyl ether T=20°C; 1 h;

1: n-PrLi / diethyl ether; tetrahydrofuran; benzene / -20 -> 20 deg C, 1.5 h 2: 1.) HMPA / 1.) ether, THF, benzene, 20 deg C, 12 h, 2.) DMSO, 100-110 deg C, 5 h 3: 6 g / hydrogen / Lindlar catalyst / hexane / 20 °C 4: 91 percent / (i-Bu)2AlH / diethyl ether / 1 h / 20 °C View Scheme

1: 1.) HMPA / 1.) ether, THF, benzene, 20 deg C, 12 h, 2.) DMSO, 100-110 deg C, 5 h 2: 6 g / hydrogen / Lindlar catalyst / hexane / 20 °C 3: 91 percent / (i-Bu)2AlH / diethyl ether / 1 h / 20 °C View Scheme

1: 6 g / hydrogen / Lindlar catalyst / hexane / 20 °C 2: 91 percent / (i-Bu)2AlH / diethyl ether / 1 h / 20 °C View Scheme

1: 1) n-BuLi, 2) HMPT / 1) THF, hexane, 10 deg C, 2) <25 deg C, 0.5 h 2: 92 percent / PPTS / ethanol / 70 °C 3: 98 percent / H2, quinoline / 5percent Pd/BaSO4 / methanol 4: 89 percent / PCC / CH2Cl2 / 1.5 h View Scheme

1: 100 percent / conc.H2SO4 / 4 h / Heating 2: 83 percent / LAH / diethyl ether / 2 h / Ambient temperature 3: 98 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 4: 1) n-BuLi, 2) HMPT / 1) THF, hexane, 10 deg C, 2) <25 deg C, 0.5 h 5: 92 percent / PPTS / ethanol / 70 °C 6: 98 percent / H2, quinoline / 5percent Pd/BaSO4 / methanol 7: 89 percent / PCC / CH2Cl2 / 1.5 h View Scheme

1: 1) Br2, 2) aq.KOH / 1) CCl4, r.t., 2) 135-145 deg C, 4 h 2: 100 percent / conc.H2SO4 / 4 h / Heating 3: 83 percent / LAH / diethyl ether / 2 h / Ambient temperature 4: 98 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 5: 1) n-BuLi, 2) HMPT / 1) THF, hexane, 10 deg C, 2) <25 deg C, 0.5 h 6: 92 percent / PPTS / ethanol / 70 °C 7: 98 percent / H2, quinoline / 5percent Pd/BaSO4 / methanol 8: 89 percent / PCC / CH2Cl2 / 1.5 h View Scheme

1: 83 percent / LAH / diethyl ether / 2 h / Ambient temperature 2: 98 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 3: 1) n-BuLi, 2) HMPT / 1) THF, hexane, 10 deg C, 2) <25 deg C, 0.5 h 4: 92 percent / PPTS / ethanol / 70 °C 5: 98 percent / H2, quinoline / 5percent Pd/BaSO4 / methanol 6: 89 percent / PCC / CH2Cl2 / 1.5 h View Scheme

1: 1) BF3*THF, 2) Jones' reagent / 1a) 0 deg C, 2 h, b) r.t., 2 h, 2) acetone, r.t., 3 h 2: 36.3 percent / Pb(OAc)4, pyridine, Cu(OAc)2 / benzene / 3 h / Heating 3: 1) Br2, 2) aq.KOH / 1) CCl4, r.t., 2) 135-145 deg C, 4 h 4: 100 percent / conc.H2SO4 / 4 h / Heating 5: 83 percent / LAH / diethyl ether / 2 h / Ambient temperature 6: 98 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 7: 1) n-BuLi, 2) HMPT / 1) THF, hexane, 10 deg C, 2) <25 deg C, 0.5 h 8: 92 percent / PPTS / ethanol / 70 °C 9: 98 percent / H2, quinoline / 5percent Pd/BaSO4 / methanol 10: 89 percent / PCC / CH2Cl2 / 1.5 h View Scheme