1: AlCl3 / tetrahydrofuran / 2 h / Ambient temperature 2: CuBr-Me2S / tetrahydrofuran; hexane / 0.33 h 3: H2 / 10percent Pd/C / methanol / 2 h / 760 Torr 4: pyridine / CH2Cl2 / 0 °C View Scheme

1: CuBr-Me2S / tetrahydrofuran; hexane / 0.33 h 2: H2 / 10percent Pd/C / methanol / 2 h / 760 Torr 3: pyridine / CH2Cl2 / 0 °C View Scheme

1: 98.6 percent / KBr, NaHCO3, 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, NaOCl / H2O / 1 h / 1 - 5 °C 2: 89.7 percent / NaHMDS / tetrahydrofuran / -90 - -71 °C 3: 99.2 percent / PCC, NaOAc, Florisil / CH2Cl2 / 20 h / Ambient temperature 4: 84.4 percent / H2SO4 / methanol; tetrahydrofuran / 22 h / 23 °C 5: 75.1 percent / NaOH / methanol / 67 h / 0 - 5 °C 6: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 7: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme

1: 89.7 percent / NaHMDS / tetrahydrofuran / -90 - -71 °C 2: 99.2 percent / PCC, NaOAc, Florisil / CH2Cl2 / 20 h / Ambient temperature 3: 84.4 percent / H2SO4 / methanol; tetrahydrofuran / 22 h / 23 °C 4: 75.1 percent / NaOH / methanol / 67 h / 0 - 5 °C 5: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 6: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme

1: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 2: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme

1: 75.1 percent / NaOH / methanol / 67 h / 0 - 5 °C 2: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 3: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme

1: 77.8 percent / DIBALH / toluene / -20 - 1 °C 2: 98.6 percent / KBr, NaHCO3, 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, NaOCl / H2O / 1 h / 1 - 5 °C 3: 89.7 percent / NaHMDS / tetrahydrofuran / -90 - -71 °C 4: 99.2 percent / PCC, NaOAc, Florisil / CH2Cl2 / 20 h / Ambient temperature 5: 84.4 percent / H2SO4 / methanol; tetrahydrofuran / 22 h / 23 °C 6: 75.1 percent / NaOH / methanol / 67 h / 0 - 5 °C 7: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 8: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme

1: 99.2 percent / PCC, NaOAc, Florisil / CH2Cl2 / 20 h / Ambient temperature 2: 84.4 percent / H2SO4 / methanol; tetrahydrofuran / 22 h / 23 °C 3: 75.1 percent / NaOH / methanol / 67 h / 0 - 5 °C 4: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 5: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme

1: 84.4 percent / H2SO4 / methanol; tetrahydrofuran / 22 h / 23 °C 2: 75.1 percent / NaOH / methanol / 67 h / 0 - 5 °C 3: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 4: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme

1: 72.6 percent / DIPEA / toluene / 5 h / 110 - 117 °C 2: 77.8 percent / DIBALH / toluene / -20 - 1 °C 3: 98.6 percent / KBr, NaHCO3, 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, NaOCl / H2O / 1 h / 1 - 5 °C 4: 89.7 percent / NaHMDS / tetrahydrofuran / -90 - -71 °C 5: 99.2 percent / PCC, NaOAc, Florisil / CH2Cl2 / 20 h / Ambient temperature 6: 84.4 percent / H2SO4 / methanol; tetrahydrofuran / 22 h / 23 °C 7: 75.1 percent / NaOH / methanol / 67 h / 0 - 5 °C 8: H2 / Pd/C / tetrahydrofuran / 21 h / 2585.7 Torr 9: 77.4 percent / CH2Cl2; dimethylsulfoxide / 2 h / -30 - -25 °C View Scheme