1.1: 0.85 g / OsO4; NaIO4; NMO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 5 h / 20 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: tetrahydrofuran; hexane / 15 h / -78 °C 3.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 4.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 5.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 6.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 8.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 9.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1.1: 1.6 g / PPh3 / CH2Cl2 / 0.5 h / -78 °C 2.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C 2.2: 99 percent / DMPU / tetrahydrofuran; various solvent(s) / 1 h 3.1: 84 percent / Li; NH3 / tetrahydrofuran / 3.33 h / -78 - -40 °C 4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 0 °C 5.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 6.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 7.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 8.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 10.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 11.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1.1: 9-BBN / tetrahydrofuran / 6 h / sonication 1.2: 88 percent / H2O2 / methanol; tetrahydrofuran; various solvent(s) 2.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 0 °C 3.1: 1.6 g / PPh3 / CH2Cl2 / 0.5 h / -78 °C 4.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C 4.2: 99 percent / DMPU / tetrahydrofuran; various solvent(s) / 1 h 5.1: 84 percent / Li; NH3 / tetrahydrofuran / 3.33 h / -78 - -40 °C 6.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 0 °C 7.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 8.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 9.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 10.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 12.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 13.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 0 °C 2.1: 1.6 g / PPh3 / CH2Cl2 / 0.5 h / -78 °C 3.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C 3.2: 99 percent / DMPU / tetrahydrofuran; various solvent(s) / 1 h 4.1: 84 percent / Li; NH3 / tetrahydrofuran / 3.33 h / -78 - -40 °C 5.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 0 °C 6.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 7.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 8.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 9.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 10.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 11.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 12.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1: 84 percent / Li; NH3 / tetrahydrofuran / 3.33 h / -78 - -40 °C 2: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 0 °C 3: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 4: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 5: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 6: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 7: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 8: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 9: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1.1: LiNH2*BH3 / tetrahydrofuran / 3.17 h 2.1: KH / various solvents / 5 h / -15 - 20 °C 3.1: 0.85 g / OsO4; NaIO4; NMO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 5 h / 20 °C 4.1: LiHMDS / tetrahydrofuran; hexane / 0.25 h / -78 °C 4.2: tetrahydrofuran; hexane / 15 h / -78 °C 5.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 6.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 7.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 8.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 10.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 11.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C 1.2: 99 percent / DMPU / tetrahydrofuran; various solvent(s) / 1 h 2.1: 84 percent / Li; NH3 / tetrahydrofuran / 3.33 h / -78 - -40 °C 3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 0 °C 4.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 5.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 6.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 7.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 9.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 10.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 2: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 3: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 4: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 5: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 6: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 7: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 2: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 2: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 3: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme