pyridine; hydrogen fluoride T=24°C; 3 h;

aluminum amalgam in tetrahydrofuran; water

hydrogen fluoride in tetrahydrofuran

1: 51 percent / Mo[N(t-Bu)(3,5-diMePh)]3/CH2Cl2 / toluene; CH2Cl2 / 9 h / 80 °C 2: 87 percent / H2; quinoline / Lindlar catalyst / hexane / 760.05 Torr 3: 88 percent / aq. HF / tetrahydrofuran / 1 h View Scheme

1: 89.5 percent / osmium tetraoxide, trimethylamine N-oxide dihydrate / tetrahydrofuran; acetone; H2O / 15 h / Ambient temperature 2: 99 percent / p-toluenesulfonic acid hydrate / 60 h 3: 99 percent / KOH / methanol / 0.5 h 4: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 5: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 6: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 7: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 53 percent / oxygen, thiourea, rose bengal / methanol / Irradiation; 1.) 3 h; 2.) in the dark without oxygen, 16 h 2: 96.4 percent / 4-(dimethylamino)pyridine / CH2Cl2; pyridine / 1.) 0 deg C,; 2.) room temperature 13 h 3: 89.5 percent / osmium tetraoxide, trimethylamine N-oxide dihydrate / tetrahydrofuran; acetone; H2O / 15 h / Ambient temperature 4: 99 percent / p-toluenesulfonic acid hydrate / 60 h 5: 99 percent / KOH / methanol / 0.5 h 6: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 7: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 8: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 9: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 99 percent / KOH / methanol / 0.5 h 2: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 3: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 4: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 5: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

tetrakis(triphenylphosphine) palladium(0) in dichloromethane T=19°C; 3 h;

1: 51 percent / Mo[N(t-Bu)(3,5-diMePh)]3/CH2Cl2 / toluene; CH2Cl2 / 9 h / 80 °C 2: 87 percent / H2; quinoline / Lindlar catalyst / hexane / 760.05 Torr 3: 88 percent / aq. HF / tetrahydrofuran / 1 h View Scheme

1: 87 percent / H2; quinoline / Lindlar catalyst / hexane / 760.05 Torr 2: 88 percent / aq. HF / tetrahydrofuran / 1 h View Scheme