1.1: sulfuric acid / tetrahydrofuran; water / 10 h / Inert atmosphere; Reflux 2.1: sodium periodate / water; isopropyl alcohol / 20 h / 0 - 20 °C / Inert atmosphere 3.1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water / 0.5 h / 0 °C / Inert atmosphere 4.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; tert-butyl alcohol / 2 h / 0 °C / Inert atmosphere 5.1: diphenylphosphoranyl azide; triethylamine / toluene / 2.5 h / 20 - 110 °C / Inert atmosphere 6.1: toluene / 7 h / 75 °C / Inert atmosphere 7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 7.2: 1 h / -78 °C / Inert atmosphere 8.1: acetic acid; zinc / ethanol / 3 h / 0 °C / Inert atmosphere 9.1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 10.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 11.1: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 12.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 13.1: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme

1: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 20 h 2: 84 percent / NaOAc, AcOH / 16 h / 50 °C 3: 92 percent / Ac2O, pyridine / 15 h / Ambient temperature 4: 97 percent / aq.OsO4, KIO4 / tetrahydrofuran; H2O / 16 h / Ambient temperature 5: 85 percent / 90percent H2O2, trifluoroacetic anhydride, KH2PO4 / CH2Cl2 / 0 °C 6: cation exchange resin AG 50W-X4 / ethanol / 50 °C 7: NaOEt / ethanol / 2 h / Ambient temperature 8: 95 percent / imidazole / dimethylformamide / Ambient temperature 9: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 10: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 11: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 12: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 13: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 14: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1.1: O3/air / CH2Cl2 / -68 - 14 °C 2.1: Et3N; DMAP / CH2Cl2; methanol / 2 h / -38 - -7 °C 3.1: methanol / 37 °C 4.1: imidazole / acetonitrile / 4 h / 20 °C 5.1: 76.1 percent / LiH / tetrahydrofuran / 21.5 h 6.1: Pd2(dba)3(CHCl3); PPh3; 1,3-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)benzene / toluene / 16 h / 40 °C 6.2: 84 percent / imidazole / dimethylformamide / 16 h / 20 °C 7.1: 94.5 percent / DIBALH / hexane / 0.5 h / -70 °C 8.1: 77.2 percent / 9-fluorenone-4-carboxylic acid / various solvent(s) / 6 h / Irradiation 9.1: triphosgene; Et3N / hexane / 1.33 h / 5 - 20 °C 10.1: 22.3 g / NaH / dimethylformamide / -45 - 0 °C View Scheme

1: 71 percent / hydrazine, Et3N / acetonitrile / 0 °C 2: 92 percent / periodinane / CH2Cl2 / Ambient temperature View Scheme

1: 71 percent / hydrazine, Et3N / acetonitrile / 0 °C 2: 92 percent / periodinane / CH2Cl2 / Ambient temperature View Scheme

1: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 20 h 2: 84 percent / NaOAc, AcOH / 16 h / 50 °C 3: 92 percent / Ac2O, pyridine / 15 h / Ambient temperature 4: 97 percent / aq.OsO4, KIO4 / tetrahydrofuran; H2O / 16 h / Ambient temperature 5: 85 percent / 90percent H2O2, trifluoroacetic anhydride, KH2PO4 / CH2Cl2 / 0 °C 6: cation exchange resin AG 50W-X4 / ethanol / 50 °C 7: NaOEt / ethanol / 2 h / Ambient temperature 8: 95 percent / imidazole / dimethylformamide / Ambient temperature 9: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 10: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 11: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 12: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 13: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 14: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme