1: 81 percent / butyl-lithium / hexane; tetrahydrofuran / 1 h / 0 °C 2: 69 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C 3: 86 percent / di-isobutylaluminum hydride / toluene / 48 h / Heating 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 5: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature View Scheme

Yield given. Multistep reaction;

1: 1.) HMPTA, n-BuLi, 3.) 4-dimethylaminopyridine 2: NaOH / diethyl ether; methanol / 0.33 h / 25 °C 3: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / 80 °C 4: 100 percent / TsOH*pyridine / methanol / 2 h / 50 °C 5: 96 percent / (COCl)2, Et3N, DMSO / CH2Cl2 / 1.5 h / -60 - -15 °C View Scheme

n-butyllithium in tetrahydrofuran; hexane 0.5 h; Ambient temperature;

1: 81 percent / butyl-lithium / hexane; tetrahydrofuran / 1 h / 0 °C 2: 82 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C 3: 79 percent / di-isobutylaluminum hydride / toluene / 48 h / Heating 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C View Scheme

1: 1.) HMPTA, n-BuLi, 3.) 4-dimethylaminopyridine 2: NaOH / diethyl ether; methanol / 0.33 h / 25 °C 3: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / 80 °C 4: 100 percent / TsOH*pyridine / methanol / 2 h / 50 °C 5: 97 percent / DMAP, pyridine / 0.33 h / 0 °C View Scheme

Yield given. Multistep reaction;

1: 81 percent / butyl-lithium / hexane; tetrahydrofuran / 1 h / 0 °C 2: 69 percent / butyl-lithium / hexane; tetrahydrofuran / 0 °C 3: 86 percent / di-isobutylaluminum hydride / toluene / 48 h / Heating 4: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C View Scheme

1: 1.) HMPTA, n-BuLi, 3.) 4-dimethylaminopyridine (DMAP) 2: NaOH / diethyl ether; methanol / 0.33 h / 25 °C 3: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / 80 °C 4: 100 percent / TsOH*pyridine / methanol / 2 h / 50 °C 5: 90 percent / DMAP, pyridine / 0.33 h / 0 °C View Scheme

Yield given. Multistep reaction. Yields of byproduct given;