1.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: tetrahydrofuran; hexane / 0.5 h 3.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 4.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 5.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 6.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 7.1: 4-dimethylaminopyridine / CH2Cl2 8.1: HCl / tetrahydrofuran / 5 h / 0 °C 9.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 10.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 11.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 12.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 12.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 13.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 14.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 15.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 15.2: CH2Cl2 / 3 h / -78 - 20 °C 16.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 17.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 18.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme