1: With pyridine; titanium(IV) isopropylate; iodine in dichloromethane T=20°C; 45 h; 2: With potassium permanganate T=0°C; 0.833333 h;

sodium iodide in tetrahydrofuran Heating;

1.1: aq. NaOH; NaBH4 / ethanol / 0.25 h 2.1: aq. KMnO4 / 2 h / cooling 2.2: 70 percent / aq. H2O2 / tetrahydrofuran / 1.17 h 3.1: 63 percent / (i-Pr)2NEt / toluene / 24 h / 85 - 89 °C View Scheme

sodium hydrogensulfide in tetrahydrofuran T=20°C; 1 h;