1: benzene 2: 2.0 M NaOH / dioxane View Scheme

sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene in tert-butyl alcohol T=20°C; 3 h;

periodic acid in diethyl ether T=0°C; 1.5 h;

View Scheme

Yield given. Multistep reaction;

1: 88 percent / 1.) lithium amide / 1.) liquid ammonia, -78 deg C, 0.5 h; 2.) HMPA, 1 h 2: 98 percent / H2 / 10 percent Pd/calcium carbonate/quinoline / hexane / 3 h / 760 Torr 3: 50 percent / m-chloroperbenzoic acid / CH2Cl2 / 2 h / 0 °C 4: 82 percent / periodic acid / diethyl ether / 1.5 h / 0 °C View Scheme

1: 98 percent / H2 / 10 percent Pd/calcium carbonate/quinoline / hexane / 3 h / 760 Torr 2: 50 percent / m-chloroperbenzoic acid / CH2Cl2 / 2 h / 0 °C 3: 82 percent / periodic acid / diethyl ether / 1.5 h / 0 °C View Scheme

1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 2: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 3: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C 2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 3.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 4.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

1: 50 percent / m-chloroperbenzoic acid / CH2Cl2 / 2 h / 0 °C 2: 82 percent / periodic acid / diethyl ether / 1.5 h / 0 °C View Scheme