1.1: (COCl)2; DMSO / CH2Cl2 / 0.33 h / -78 °C 1.2: 75 percent / CH2Cl2 / 3 h / 25 °C 2.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C 3.1: MsCl; Et3N / CH2Cl2 / 1 h / -40 °C 3.2: 71 percent / LiCl / tetrahydrofuran; CH2Cl2 / 3 h / 20 °C 4.1: 70 percent / DIBAL-H / CH2Cl2; hexane / 3 h / -78 °C 5.1: NaH / tetrahydrofuran / 1 h / 20 °C 5.2: 53 percent / tetrahydrofuran / 12 h / 70 °C 6.1: (-)-sparteine; nBuLi / toluene; hexane / 1.5 h / -78 °C 7.1: TMEDA; tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C 7.2: tetrahydrofuran; pentane / -78 °C 8.1: 93 mg / 1,2-dichloro-ethane / 3 h / Heating 9.1: 55 percent / MeSO3H; H2O / 16 h / Heating 10.1: Jones reagent / acetone / 0.08 h / 0 °C 11.1: 8.0 mg / aq. NaOH / methanol / 18 h / Heating View Scheme

1.1: (-)-sparteine; nBuLi / toluene; hexane / 1.5 h / -78 °C 2.1: TMEDA; tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C 2.2: tetrahydrofuran; pentane / -78 °C 3.1: 93 mg / 1,2-dichloro-ethane / 3 h / Heating 4.1: 55 percent / MeSO3H; H2O / 16 h / Heating 5.1: Jones reagent / acetone / 0.08 h / 0 °C 6.1: 8.0 mg / aq. NaOH / methanol / 18 h / Heating View Scheme

1: 93 mg / 1,2-dichloro-ethane / 3 h / Heating 2: 55 percent / MeSO3H; H2O / 16 h / Heating 3: Jones reagent / acetone / 0.08 h / 0 °C 4: 8.0 mg / aq. NaOH / methanol / 18 h / Heating View Scheme

1.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C 2.1: MsCl; Et3N / CH2Cl2 / 1 h / -40 °C 2.2: 71 percent / LiCl / tetrahydrofuran; CH2Cl2 / 3 h / 20 °C 3.1: 70 percent / DIBAL-H / CH2Cl2; hexane / 3 h / -78 °C 4.1: NaH / tetrahydrofuran / 1 h / 20 °C 4.2: 53 percent / tetrahydrofuran / 12 h / 70 °C 5.1: (-)-sparteine; nBuLi / toluene; hexane / 1.5 h / -78 °C 6.1: TMEDA; tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C 6.2: tetrahydrofuran; pentane / -78 °C 7.1: 93 mg / 1,2-dichloro-ethane / 3 h / Heating 8.1: 55 percent / MeSO3H; H2O / 16 h / Heating 9.1: Jones reagent / acetone / 0.08 h / 0 °C 10.1: 8.0 mg / aq. NaOH / methanol / 18 h / Heating View Scheme

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 3.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 4.2: 0.5 h / -20 °C / Inert atmosphere 5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 6.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 8.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 9.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 9.2: 20 °C / Inert atmosphere View Scheme

1.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 2.2: 0.5 h / -20 °C / Inert atmosphere 3.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 4.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 5.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 6.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 7.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 7.2: 20 °C / Inert atmosphere View Scheme

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 1.2: 0.5 h / -20 °C / Inert atmosphere 2.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 3.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 4.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 5.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 6.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 6.2: 20 °C / Inert atmosphere View Scheme

1.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 2.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 4.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 5.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 5.2: 20 °C / Inert atmosphere View Scheme

1.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 2.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 3.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere View Scheme

1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 2.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere View Scheme