osmium(VIII) oxide; 4-methylmorpholine N-oxide in water; acetone; tert-butyl alcohol T=20°C; 72 h;

periodic acid in tetrahydrofuran T=0 - 5°C; 1 h;

1.1: 99 percent / periodic acid dihydrate / tetrahydrofuran / 1 h / 0 - 5 °C 2.1: magnesium; iodine / tetrahydrofuran / 60 °C 2.2: 38 percent / tetrahydrofuran / 48 h / cooling 3.1: pyridine / CH2Cl2 / 72 h / cooling 4.1: lithium aluminum hydride / tetrahydrofuran / 1.5 h / Heating 5.1: 1.52 g / hydrochloric acid / H2O / 0.5 h / Heating 6.1: 73.5 percent / sodium acetate; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH2Cl2 / 2.33 h / 0 - 20 °C 7.1: magnesium / tetrahydrofuran 7.2: 73 percent / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme