sodium hydroxide in acetone 48 h; Heating; Yield given;

1.1: water; potassium hydroxide / methanol / 70 °C 2.1: triethylamine / tetrahydrofuran / -70 - 0 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / -70 °C / Inert atmosphere 3.2: -70 - 0 °C / Inert atmosphere 4.1: potassium hexamethylsilazane / tetrahydrofuran; hexane / 1.17 h / -72 °C / Inert atmosphere 4.2: 2 h / -72 °C / Inert atmosphere 5.1: lithium borohydride / methanol; diethyl ether / 20 °C 6.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 20 °C 7.1: Fetizon's reagent (silver carbonate on celite) / benzene / 4 h / Reflux 8.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 8.2: 22 h / -78 - -50 °C / Inert atmosphere 9.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr / Inert atmosphere View Scheme

1.1: water; potassium hydroxide / methanol / 70 °C 2.1: triethylamine / tetrahydrofuran / -70 - 0 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / -70 °C / Inert atmosphere 3.2: -70 - 0 °C / Inert atmosphere 4.1: potassium hexamethylsilazane / tetrahydrofuran; hexane / 1.17 h / -72 °C / Inert atmosphere 4.2: 2 h / -72 °C / Inert atmosphere 5.1: lithium borohydride / methanol; diethyl ether / 20 °C 6.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 20 °C 7.1: Fetizon's reagent (silver carbonate on celite) / benzene / 4 h / Reflux 8.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 8.2: 22 h / -78 - -50 °C / Inert atmosphere 9.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr / Inert atmosphere 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -15 °C View Scheme

1: 20percent aq. NaOH / acetone / 48 h / Heating 2: 1.)LDA, 2.) I2 / 1.) THF, from -78 deg C to RT, 5 h, 2.) THF, from -78 deg C to RT, 18 h 3: Ac2O / 24 h / Heating 4: 24 h / 80 °C 5: 1.) BH3*THF, 2) aq. HCl / 1.) THF, from -17 deg C to RT, 185 min, 2.)0 degC, 1h View Scheme

1.1: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C 2.1: oxalyl chloride / CH2Cl2 / 20 h / 20 °C 3.1: tetrahydrofuran; hexane; acetonitrile / 4 h 4.1: 183 mg / rhodium (II) acetate dimer / CH2Cl2 / 1 h / Heating 5.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 5.2: 20 percent / CHCl3 / 1 h / Heating 6.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme

1: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C 2: oxalyl chloride / CH2Cl2 / 20 h / 20 °C 3: tetrahydrofuran; hexane; acetonitrile / 4 h View Scheme

Multi-step reaction with 2 steps 1: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C2: oxalyl chloride / CH2Cl2 / 20 h / 20 °C