1: 97 percent / dimethylformamide 2: 93 percent / DIBAL / CH2Cl2 / -78 °C 3: 80 percent / (+)-DIPT, Ti(Oi-Pr)4, TBHP / CH2Cl2 / -20 °C 4: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C 5: 73 percent / KHMDS / tetrahydrofuran; toluene 6: 88 percent / DDQ / CH2Cl2; H2O 7: 88 percent / i-Pr2NEt / CH2Cl2 / 0 °C 8: 76 percent / p-toluenesulfonic acid / dimethylsulfoxide / 120 °C 9: 1.) OsO4, NMO; 2.) NaIO4 / 1.) t-BuOH, THF, H2O; 2.) THF, H2O 10: LiAlH4 / tetrahydrofuran / 0 °C 11: 87 percent / TFA / methanol 12: 89 percent / H2 / Pd/C / ethanol View Scheme

1: 97 percent / p-toluenesulfonic acid / dimethylformamide 2: 93 percent / diisobutylaluminum hydride / CH2Cl2 / 0.5 h / -78 °C 3: 80 percent / Ti(Oi-Pr)4; (+)-diisopropyl tartrate; t-BuOOH / CH2Cl2 / -20 °C 4: 97 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 16 h / 20 °C 5: 92 percent / 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile / CH2Cl2; H2O / 3 h / 20 °C 6: 100 percent / diisopropylethylamine / CH2Cl2 / 20 °C 7: 91 percent / NaN3 / dimethylformamide / 80 °C 8: 83 percent / triphenylphosphine / tetrahydrofuran; H2O / 20 °C 9: 90 percent / ethanol / 65 h / Heating 10: 82 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -78 °C 11: 97 percent / potassium carbonate / acetonitrile / 5 h / Heating 12: 100 percent / tetra-n-butylammonium fluoride dihydrate / tetrahydrofuran / 14 h / 20 °C 13: (COCl)2; triethylamine / dimethylsulfoxide; CH2Cl2 / -78 - 20 °C 14: 71 percent / TiCl4 / CH2Cl2 / 15 h / -78 °C 15: OsO4; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 16: 45 mg / NaHCO3; NaIO4 / tetrahydrofuran; H2O / 3 h / 20 °C 17: 81 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 24 h / 20 °C View Scheme

1: 97 percent / p-toluenesulfonic acid / dimethylformamide 2: 93 percent / diisobutylaluminum hydride / CH2Cl2 / 0.5 h / -78 °C 3: 80 percent / Ti(Oi-Pr)4; (+)-diisopropyl tartrate; t-BuOOH / CH2Cl2 / -20 °C 4: 97 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 16 h / 20 °C 5: 92 percent / 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile / CH2Cl2; H2O / 3 h / 20 °C 6: 100 percent / diisopropylethylamine / CH2Cl2 / 20 °C 7: 91 percent / NaN3 / dimethylformamide / 80 °C 8: 83 percent / triphenylphosphine / tetrahydrofuran; H2O / 20 °C 9: 90 percent / ethanol / 65 h / Heating 10: 100 percent / hydrochloric acid / methanol; H2O / 4 h / 70 °C View Scheme

1: 97 percent / p-toluenesulfonic acid / dimethylformamide 2: 93 percent / diisobutylaluminum hydride / CH2Cl2 / 0.5 h / -78 °C 3: 80 percent / Ti(Oi-Pr)4; (+)-diisopropyl tartrate; t-BuOOH / CH2Cl2 / -20 °C 4: 97 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 16 h / 20 °C 5: 92 percent / 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile / CH2Cl2; H2O / 3 h / 20 °C 6: 100 percent / diisopropylethylamine / CH2Cl2 / 20 °C 7: 91 percent / NaN3 / dimethylformamide / 80 °C 8: 83 percent / triphenylphosphine / tetrahydrofuran; H2O / 20 °C 9: 90 percent / ethanol / 65 h / Heating 10: 100 percent / hydrochloric acid / methanol; H2O / 4 h / 70 °C View Scheme