1: K2[OsO2(OH)4]; 1,4-bis(dihydroquininyl)anthraquinone / propan-1-ol; H2O / 20 °C 2: Ti(OiPr)4 / 20 °C 3: H2 / Pd/C / methanol 4: 85 percent / TsOH / 1,2-dimethoxy-ethane / 4 h 5: 85 percent / LHMDS / tetrahydrofuran / -78 °C 6: dicyclohexylcarbodiimide; DMSO; CF3COOH / pyridine 7: 60 percent / TiCl4 / -78 - 35 °C 8: O3; Me2S 9: NaClO2; NaH2PO4 10: HCOONH4 / Pd black 11: NaOH; H2O View Scheme

1: H2 / Pd/C / methanol 2: 85 percent / TsOH / 1,2-dimethoxy-ethane / 4 h 3: 85 percent / LHMDS / tetrahydrofuran / -78 °C 4: dicyclohexylcarbodiimide; DMSO; CF3COOH / pyridine 5: 60 percent / TiCl4 / -78 - 35 °C 6: O3; Me2S 7: NaClO2; NaH2PO4 8: HCOONH4 / Pd black 9: NaOH; H2O View Scheme

1: Ti(OiPr)4 / 20 °C 2: H2 / Pd/C / methanol 3: 85 percent / TsOH / 1,2-dimethoxy-ethane / 4 h 4: 85 percent / LHMDS / tetrahydrofuran / -78 °C 5: dicyclohexylcarbodiimide; DMSO; CF3COOH / pyridine 6: 60 percent / TiCl4 / -78 - 35 °C 7: O3; Me2S 8: NaClO2; NaH2PO4 9: HCOONH4 / Pd black 10: NaOH; H2O View Scheme

1: 1.) i-Pr2NEt, H2 / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h 2: 48percent HF / acetonitrile / 24 h / 23 °C 3: Et3N, oxalyl chloride, DMSO / CH2Cl2 / 2 h / -78 °C 4: 1.) NaClO2, 20percent aq. NaH2PO4, 2.) 1,3-propanedithiol, HCl / 1.) t-BuOH, 2-methyl-2-butene, 23 deg C, 1 h, 2.) CF3CH2OH, 50-55 deg C, 7.5 h View Scheme

1: 1.) LDA, 2.) LDA, PhSeBr, 3.) O3 2: 89 percent / 2,6-lutidine / CH2Cl2 / Ambient temperature 3: 55 percent / SnCl4 / diethyl ether / -78 °C 4: 99 percent / pyridine / Ambient temperature 5: 87 percent / OsO4, N-methylmorpholine N-oxide / acetone; H2O / Ambient temperature 6: 91 percent / tetrahydrofuran / Ambient temperature 7: 94 percent / Bu3SnH, AIBN / toluene / Heating 8: 1.) 2 N aq. NaOH, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) MeOH, 0-3 deg C, 2.) MeOH, RT 9: pyridine 10: pyridine / Ambient temperature 11: 91 percent / HF / acetonitrile / Ambient temperature 12: 91 percent / Jones' reagent / acetone / 0 - 20 °C 13: 100 percent / 0.2 N aq. NaOH / Ambient temperature View Scheme

1: 89 percent / 2,6-lutidine / CH2Cl2 / Ambient temperature 2: 55 percent / SnCl4 / diethyl ether / -78 °C 3: 99 percent / pyridine / Ambient temperature 4: 87 percent / OsO4, N-methylmorpholine N-oxide / acetone; H2O / Ambient temperature 5: 91 percent / tetrahydrofuran / Ambient temperature 6: 94 percent / Bu3SnH, AIBN / toluene / Heating 7: 1.) 2 N aq. NaOH, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) MeOH, 0-3 deg C, 2.) MeOH, RT 8: pyridine 9: pyridine / Ambient temperature 10: 91 percent / HF / acetonitrile / Ambient temperature 11: 91 percent / Jones' reagent / acetone / 0 - 20 °C 12: 100 percent / 0.2 N aq. NaOH / Ambient temperature View Scheme

1: 55 percent / SnCl4 / diethyl ether / -78 °C 2: 99 percent / pyridine / Ambient temperature 3: 87 percent / OsO4, N-methylmorpholine N-oxide / acetone; H2O / Ambient temperature 4: 91 percent / tetrahydrofuran / Ambient temperature 5: 94 percent / Bu3SnH, AIBN / toluene / Heating 6: 1.) 2 N aq. NaOH, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) MeOH, 0-3 deg C, 2.) MeOH, RT 7: pyridine 8: pyridine / Ambient temperature 9: 91 percent / HF / acetonitrile / Ambient temperature 10: 91 percent / Jones' reagent / acetone / 0 - 20 °C 11: 100 percent / 0.2 N aq. NaOH / Ambient temperature View Scheme

1: 87 percent / OsO4, N-methylmorpholine N-oxide / acetone; H2O / Ambient temperature 2: 91 percent / tetrahydrofuran / Ambient temperature 3: 94 percent / Bu3SnH, AIBN / toluene / Heating 4: 1.) 2 N aq. NaOH, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) MeOH, 0-3 deg C, 2.) MeOH, RT 5: pyridine 6: pyridine / Ambient temperature 7: 91 percent / HF / acetonitrile / Ambient temperature 8: 91 percent / Jones' reagent / acetone / 0 - 20 °C 9: 100 percent / 0.2 N aq. NaOH / Ambient temperature View Scheme

1: 97 percent / imidazole / dimethylformamide / 3.5 h / 23 °C 2: 96 percent / TsOH / benzene / 0.5 h / Heating 3: LiBH4 / tetrahydrofuran; methanol / 24 h / 23 °C 4: DMSO, (COCl)2, Et3N / CH2Cl2 / 1.5 h / -78 °C 5: 1.) LDA / 1.) THF, -78 deg C 6: 87 percent / H2 / Pd/C / ethanol / 24 h / 23 °C 7: 90 percent / 5percent HF / acetonitrile / 9 h / 23 °C 8: 73 percent / DMSO, (COCl)2, Et3N / CH2Cl2 / 2 h / -78 °C 9: 95 percent / NaClO2, NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s) / 0.25 h / 23 °C 10: 95 percent / 1,3-propanedithiol, 2percent HCl (gas) / various solvent(s) / 6 h / 50 °C View Scheme

1: 91 percent / TfOH / methanol / 6.5 h / 80 °C 2: 97 percent / imidazole / dimethylformamide / 3.5 h / 23 °C 3: 96 percent / TsOH / benzene / 0.5 h / Heating 4: LiBH4 / tetrahydrofuran; methanol / 24 h / 23 °C 5: DMSO, (COCl)2, Et3N / CH2Cl2 / 1.5 h / -78 °C 6: 1.) LDA / 1.) THF, -78 deg C 7: 87 percent / H2 / Pd/C / ethanol / 24 h / 23 °C 8: 90 percent / 5percent HF / acetonitrile / 9 h / 23 °C 9: 73 percent / DMSO, (COCl)2, Et3N / CH2Cl2 / 2 h / -78 °C 10: 95 percent / NaClO2, NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s) / 0.25 h / 23 °C 11: 95 percent / 1,3-propanedithiol, 2percent HCl (gas) / various solvent(s) / 6 h / 50 °C View Scheme