dimethyl sulfoxide in dichloromethane; trifluoroacetic acid T=-78°C;

1.1: triethylamine / CH2Cl2 / 1.5 h / 0 °C 2.1: 84 percent / DBU / 2 h / 80 °C 3.1: 47 percent / H2 / 10 percent Pd/C / ethanol / 4 h / 0 - 10 °C / 760 Torr 4.1: lithium perchlorate / diethyl ether / 168 h / 20 °C 5.1: 96 percent / H2 / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr 6.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C 7.1: 83 percent / DBU / toluene / 5 h / 100 °C 8.1: 96 percent / H2 / PtO2 / ethanol / 16 h / 20 °C / 760 Torr 9.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C 10.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C 11.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C 12.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C 13.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C 13.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 14.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 15.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 16.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 17.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 17.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 18.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 19.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 20.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 21.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme