1.1: TMSOTf / CH2Cl2; petroleum ether / 2 h 2.1: 2.70 g / NaOMe / methanol / 3 h / 20 °C 3.1: 73.3 percent / DMAP; Et3N / CH2Cl2 / 20 °C 4.1: 86.1 percent / dimethylsulfoxide / 20 °C 5.1: 72.4 percent / cateholborane / 36 h / 20 °C 6.1: 95.4 percent / I2; aq. NaOH / diethyl ether / 0.33 h / 20 °C 7.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 7.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 7.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 8.1: 131 mg / (S)-2-methyl-CBS-oxazaborolidine; BH3*Me2S / tetrahydrofuran; toluene / 0.25 h / 0 °C 9.1: 96.4 percent / diethyl ether / 1 h / 0 °C 10.1: 72 percent / Li-naphthalene / tetrahydrofuran / -25 °C 11.1: MnO2 / CH2Cl2 / 3 h / Heating 12.1: 33.6 mg / NaH2PO4; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O / 20 °C 13.1: NEt3; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 6 h 13.2: 81 percent / DMAP / tetrahydrofuran; toluene / Heating 14.1: 91 percent / aq. HCl / tetrahydrofuran; H2O / 48 h / 20 °C View Scheme