1: 98 percent / benzene / 1 h / Heating 2: acetic acid; methanol / 2 h / 200 °C 3: magnesium sulfate / CH2Cl2 / 0.02 h / 20 °C 4: 63 percent / benzene / 0.17 h / Heating 5: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 6: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 7: pyridine / 15 h / 20 °C 8: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 9: trifluoroacetic acid / CH2Cl2 / 0.5 h 10: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 11: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 12: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 13: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: NaH / tetrahydrofuran / 2 h / 67 °C 2: magnesium sulfate / CH2Cl2 / 0.02 h / 20 °C 3: 63 percent / benzene / 0.17 h / Heating 4: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 5: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 6: pyridine / 15 h / 20 °C 7: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 8: trifluoroacetic acid / CH2Cl2 / 0.5 h 9: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 10: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 11: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 12: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: NaH / tetrahydrofuran / 2 h / 67 °C 2: magnesium sulfate / CH2Cl2 / 0.02 h / 20 °C 3: 63 percent / benzene / 0.17 h / Heating 4: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 5: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 6: pyridine / 15 h / 20 °C 7: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 8: trifluoroacetic acid / CH2Cl2 / 0.5 h 9: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 10: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 11: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 12: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: 98 percent / benzene / 1 h / Heating 2: acetic acid; methanol / 2 h / 200 °C 3: magnesium sulfate / CH2Cl2 / 0.02 h / 20 °C 4: 63 percent / benzene / 0.17 h / Heating 5: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 6: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 7: pyridine / 15 h / 20 °C 8: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 9: trifluoroacetic acid / CH2Cl2 / 0.5 h 10: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 11: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 12: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 13: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: magnesium sulfate / CH2Cl2 / 0.02 h / 20 °C 2: 63 percent / benzene / 0.17 h / Heating 3: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 4: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 5: pyridine / 15 h / 20 °C 6: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 7: trifluoroacetic acid / CH2Cl2 / 0.5 h 8: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 9: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 10: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 11: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: 63 percent / benzene / 0.17 h / Heating 2: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 3: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 4: pyridine / 15 h / 20 °C 5: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 6: trifluoroacetic acid / CH2Cl2 / 0.5 h 7: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 8: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 9: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 10: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 2: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 3: pyridine / 15 h / 20 °C 4: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 5: trifluoroacetic acid / CH2Cl2 / 0.5 h 6: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 7: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 8: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 9: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: acetic acid; methanol / 2 h / 200 °C 2: magnesium sulfate / CH2Cl2 / 0.02 h / 20 °C 3: 63 percent / benzene / 0.17 h / Heating 4: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 5: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 6: pyridine / 15 h / 20 °C 7: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 8: trifluoroacetic acid / CH2Cl2 / 0.5 h 9: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 10: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 11: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 12: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: 61 percent / 50percent aq. acetic acid / 2 h / 200 °C 2: NaH / tetrahydrofuran / 2 h / 67 °C 3: 63 percent / benzene / 0.17 h / Heating 4: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 5: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 6: pyridine / 15 h / 20 °C 7: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 8: trifluoroacetic acid / CH2Cl2 / 0.5 h 9: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 10: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 11: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 12: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: 91 percent / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) 20 deg C, 1 h 2: 97 percent / 30percent hydrogen peroxide / CH2Cl2 / 0.5 h 3: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 4: pyridine / 15 h / 20 °C 5: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 6: trifluoroacetic acid / CH2Cl2 / 0.5 h 7: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 8: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 9: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 10: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme