1.1: 81 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 1 h / 20 °C 2.1: n-BuLi / tetrahydrofuran / 0.17 h / 0 °C 2.2: 68 percent / tetrahydrofuran / 20 °C 3.1: 76 percent / Oxone; OsO4 / dimethylformamide / 20 °C View Scheme

1: α,α'-dihydroxy-o-xylene With sodium hydride in tetrahydrofuran T=0°C; 16 h; 2: tert-butyldimethylsilyl chloride in tetrahydrofuran T=20°C; 1 h; Further stages.;

pyridine in dichloromethane 8 h; Ambient temperature;

1: sodium hydride; α,α'-dihydroxy-o-xylene in tetrahydrofuran; mineral oil T=20°C; 2: tert-butyldimethylsilyl chloride in tetrahydrofuran; mineral oil T=0 - 20°C; 1.66667 h;

in ethyl acetate; N,N-dimethyl-formamide

1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 25 °C / 760.05 Torr / |Inert atmosphere 2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 25 °C / 760.05 Torr / |Inert atmosphere View Scheme