1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice 2: acetic acid / water / 16 h / 20 °C 3: sodium periodate / 1,4-dioxane; water / 1 h View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / |Cooling with ice 2.1: acetic acid / water / 16 h / 20 °C 3.1: sodium periodate / water; 1,4-dioxane / 1 h 4.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / |Cooling with ice 5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C 6.1: pyridine / monofluorodichloromethane / 2 h / 20 °C 7.1: acetic acid; sulfuric acid / water / 2 h / 20 °C 8.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / 55 °C 8.2: 5.5 h / 0 - 55 °C 9.1: potassium carbonate / methanol / 5 h / 20 °C 10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 20 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1: 70percent aq. acetic acid / 16 h / Ambient temperature 2: 85.8 percent / pyridine / 96 h / Ambient temperature 3: 83 percent / NaI / butan-2-one / 18 h / Heating 4: 1.)I2, silver trifluoroacetate 2.) H2, W-4 Raney nickel, triethylamine / 1.)DME, r.t., 15 min; 2.) MeOH, 3 h, 0.3-0.35 MPa 5: 91 percent / NaOMe / methanol / 10 h / 5 - 20 °C / Irradiation 6: 89 percent / pyridine 7: 83 percent / acetolysis 8: 62 percent / tin(IV) chloride 9: 84 percent / deacylation 10: 49 percent / diphenylcarbonate, NaHCO3 / dimethylformamide / 0.42 h / 144 - 145 °C View Scheme

1: 70percent aq. acetic acid / 16 h / Ambient temperature 2: 85.8 percent / pyridine / 96 h / Ambient temperature 3: 83 percent / NaI / butan-2-one / 18 h / Heating 4: 1.)I2, silver trifluoroacetate 2.) H2, W-4 Raney nickel, triethylamine / 1.)DME, r.t., 15 min; 2.) MeOH, 3 h, 0.3-0.35 MPa 5: 91 percent / NaOMe / methanol / 10 h / 5 - 20 °C / Irradiation 6: 89 percent / pyridine 7: 83 percent / acetolysis 8: 62 percent / tin(IV) chloride 9: 84 percent / deacylation View Scheme

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