D-glucose; water T=35°C; bakers' yeast, pH 5-5.2;

Grubb's 2nd generation catalyst in dichloromethane T=40°C; 3 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;

dipyridinium dichromate in dichloromethane T=20°C;

(SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium in toluene T=20°C; 0.5 h;

1: 90 percent / H2; quinoline / Pd-Pb/CaCO3 / benzene / 12 h / 24 °C / 760 Torr 2: 100 percent / pyridinium dichromate; MS 3 Angstroem; AcOH / CH2Cl2 / 0.5 h / 25 °C View Scheme

1: pyridine / 14 h / 20 °C 2: 42 percent / K2CO3 / 0.5 h / 70 °C 3: 90 percent / H2; quinoline / Pd-Pb/CaCO3 / benzene / 12 h / 24 °C / 760 Torr 4: 100 percent / pyridinium dichromate; MS 3 Angstroem; AcOH / CH2Cl2 / 0.5 h / 25 °C View Scheme