1.1: Mg / diethyl ether / 2 h / Heating 1.2: 43 percent / Li2CuCl4 / diethyl ether; tetrahydrofuran / 2 h / -78 °C 2.1: nBuLi / diethyl ether; various solvent(s) / 0.17 h / -40 °C 2.2: 85 percent / diethyl ether / 12 h / -18 °C 3.1: 76 percent / EtMgBr; i-PrOH / CH2Cl2 / 18 h / 20 °C 4.1: 90 percent / diisopropylethylamine / CH2Cl2 / 0.42 h / 0 °C 5.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 5.2: 87 percent / tetrahydrofuran / -78 - 20 °C 6.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 7.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 8.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 9.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 10.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 11.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 12.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 13.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 14.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 15.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 16.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 17.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 18.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 19.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 20.1: 2,4,6-trichlorobenzoyl chloride; Et3N 20.2: 74 percent / 4-dimethylaminopyridine 21.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 22.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme