1: CrCl2 / tetrahydrofuran / 3 h / Ambient temperature 2: 89 percent / 10-camforsulfonic acid / methanol / 60 °C 3: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 4: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 5: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 6: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 7: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 8: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: DIBAL-H / CH2Cl2 / -78 °C 2: CrCl2 / tetrahydrofuran / 3 h / Ambient temperature 3: 89 percent / 10-camforsulfonic acid / methanol / 60 °C 4: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 5: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 6: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 7: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 8: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 9: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: MeONa / methanol 2: 10-camphosulfonic acid / 0 °C 3: pyridine 4: 15-crown-5 / dimethylformamide / 60 °C 5: DIBAL-H / CH2Cl2 / -78 °C 6: CrCl2 / tetrahydrofuran / 3 h / Ambient temperature 7: 89 percent / 10-camforsulfonic acid / methanol / 60 °C 8: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 9: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 10: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 11: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 12: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 13: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: aq. NaIO4 / acetone / 0 °C 2: NaBH4 / methanol / 0 °C 3: MeONa / methanol 4: 10-camphosulfonic acid / 0 °C 5: pyridine 6: 15-crown-5 / dimethylformamide / 60 °C 7: DIBAL-H / CH2Cl2 / -78 °C 8: CrCl2 / tetrahydrofuran / 3 h / Ambient temperature 9: 89 percent / 10-camforsulfonic acid / methanol / 60 °C 10: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 11: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 12: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 13: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 14: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 15: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 96 percent / 10-camphorsulfonic acid / methanol / Ambient temperature 2: aq. NaIO4 / acetone / 0 °C 3: NaBH4 / methanol / 0 °C 4: MeONa / methanol 5: 10-camphosulfonic acid / 0 °C 6: pyridine 7: 15-crown-5 / dimethylformamide / 60 °C 8: DIBAL-H / CH2Cl2 / -78 °C 9: CrCl2 / tetrahydrofuran / 3 h / Ambient temperature 10: 89 percent / 10-camforsulfonic acid / methanol / 60 °C 11: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 12: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 13: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 14: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 15: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 16: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 15-crown-5 / dimethylformamide / 60 °C 2: DIBAL-H / CH2Cl2 / -78 °C 3: CrCl2 / tetrahydrofuran / 3 h / Ambient temperature 4: 89 percent / 10-camforsulfonic acid / methanol / 60 °C 5: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 6: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 7: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 8: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 9: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 10: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 93 percent / MeONa / methanol 2: CH2Cl2; hexane / Ambient temperature 3: pyridine, DMAP / Ambient temperature 4: 96 percent / 10-camphorsulfonic acid / methanol / Ambient temperature 5: aq. NaIO4 / acetone / 0 °C 6: NaBH4 / methanol / 0 °C 7: MeONa / methanol 8: 10-camphosulfonic acid / 0 °C 9: pyridine 10: 15-crown-5 / dimethylformamide / 60 °C 11: DIBAL-H / CH2Cl2 / -78 °C 12: CrCl2 / tetrahydrofuran / 3 h / Ambient temperature 13: 89 percent / 10-camforsulfonic acid / methanol / 60 °C 14: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 15: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 16: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 17: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 18: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 19: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1.1: KH / tetrahydrofuran / 0.5 h / -5 °C 1.2: 92 percent / tetrahydrofuran / 2.5 h / 20 °C 2.1: 9-BBN / tetrahydrofuran / 6 h / sonication 2.2: 88 percent / H2O2 / methanol; tetrahydrofuran; various solvent(s) 3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 0 °C 4.1: 1.6 g / PPh3 / CH2Cl2 / 0.5 h / -78 °C 5.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C 5.2: 99 percent / DMPU / tetrahydrofuran; various solvent(s) / 1 h 6.1: 84 percent / Li; NH3 / tetrahydrofuran / 3.33 h / -78 - -40 °C 7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 0 °C 8.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 9.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 10.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 11.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 13.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 14.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme

1.1: KH / various solvents / 5 h / -15 - 20 °C 2.1: 0.85 g / OsO4; NaIO4; NMO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 5 h / 20 °C 3.1: LiHMDS / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: tetrahydrofuran; hexane / 15 h / -78 °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

1.1: LiHMDS / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: tetrahydrofuran; hexane / 15 h / -78 °C 2.1: 398 mg / BF3*Et2O / CH2Cl2 / 1 h / -90 °C 3.1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 4.1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 5.1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 6.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 7.1: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 8.1: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme