jones reagent T=0°C;

pyridine in diethyl ether T=0 - 10°C; 24 h;

hydrogenchloride in methanol Ambient temperature;

baker's yeast; D-glucose in water T=20°C; 96 h;

1: triethylamine / CH2Cl2 / 1 h / 0 °C 2: 243 g / PTSA / CH2Cl2 / 4 h / 20 °C 3: 67 percent / Et2NH*HCl; hydroquinone / H2O / 3 h / 100 °C 4: 88 percent / PTSA; hydroquinone / 72 h / 50 °C 5: MCPBA / CH2Cl2 / -78 - 20 °C 6: 56 g / PTSA / tetrahydrofuran; H2O / 2 h / 20 °C 7: 40 percent / baker's yeast; XAD; glucose / H2O / 96 h / 20 °C View Scheme

1: MCPBA / CH2Cl2 / -78 - 20 °C 2: 56 g / PTSA / tetrahydrofuran; H2O / 2 h / 20 °C 3: 40 percent / baker's yeast; XAD; glucose / H2O / 96 h / 20 °C View Scheme

1: 58 percent / sulfuryl cloride / CH2Cl2 / Heating; 1.) 15 min; 2.) reflux 30 min 2: 100 percent / formic acid / 48 h / Heating 3: 63 percent / 1N HCl / methanol / Ambient temperature View Scheme