ammonium acetate T=50°C; 12 h;

1: 94 percent / pyridine / 1.5 h / Heating 2: 86 percent / selenium dioxide / bis-(2-methoxy-ethyl) ether / 1.5 h / 160 °C 3: 90 percent / ammonium acetate / 12 h / 50 °C View Scheme

1: CHCl3 / 0.5 h / Ambient temperature 2: LDA / tetrahydrofuran / Ambient temperature; 1.) -78 deg C, 2.) RT, 10 h 3: 1.) RhCl3*3H2O, 2.) conc. HCl / 1.) ethanol, reflux, 14 h, 2.) reflux, 20 min 4: 94 percent / pyridine / 1.5 h / Heating 5: 86 percent / selenium dioxide / bis-(2-methoxy-ethyl) ether / 1.5 h / 160 °C 6: 90 percent / ammonium acetate / 12 h / 50 °C View Scheme

1: 1.) RhCl3*3H2O, 2.) conc. HCl / 1.) ethanol, reflux, 14 h, 2.) reflux, 20 min 2: 94 percent / pyridine / 1.5 h / Heating 3: 86 percent / selenium dioxide / bis-(2-methoxy-ethyl) ether / 1.5 h / 160 °C 4: 90 percent / ammonium acetate / 12 h / 50 °C View Scheme

1: 86 percent / selenium dioxide / bis-(2-methoxy-ethyl) ether / 1.5 h / 160 °C 2: 90 percent / ammonium acetate / 12 h / 50 °C View Scheme

1: 74 percent / selenium dioxide / bis-(2-methoxy-ethyl) ether / Heating 2: 90 percent / ammonium acetate / 12 h / 50 °C View Scheme

1: 74 percent / LDA / tetrahydrofuran / 1) -78 deg C, 30 min, 2) -78 deg C to room temp., 10 h 2: 1) RhCl3*3H2O, 2) 6N HCl / 1) EtOH, reflux, 14 h, 2) rflux, 20 min. 3: pyridine 4: SeO2 / bis-(2-methoxy-ethyl) ether / 2 h / 160 °C / in sealed tube 5: 90 percent / NH4OAc / 12 h / 50 °C View Scheme