1: periodic acid / tetrahydrofuran; H2O / 8 h / 25 °C 2: 92 percent / AcOOH; NaOAc / ethyl acetate / 20 h / 20 °C 3: 49 percent / aq. H2O2; aq. H2SO4 / ethyl acetate / 20 h / 20 °C View Scheme

1.1: 1 N aq. NaOH / 2-methyl-propan-2-ol / 20 °C 1.2: H2SO4 / ethyl acetate / 2 h / 0 - 20 °C 2.1: 97 percent / NaIO4 / tetrahydrofuran; H2O / 16 h / 20 °C 3.1: 95 percent / peracetic acid / 50 - 55 °C 4.1: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 5.1: 96 percent / n-BuLi; TsCl / hexane; tetrahydrofuran / 0 - 20 °C View Scheme

1: periodic acid / tetrahydrofuran; H2O / 8 h / 25 °C 2: 92 percent / AcOOH; NaOAc / ethyl acetate / 20 h / 20 °C 3: 30 percent / AcOOH / ethyl acetate / 2 h / 15 °C View Scheme