1: 96 percent / aq. acetic acid / 15 h / Ambient temperature 2: 97 percent / NaH / tetrahydrofuran / 0 °C 3: 1.) t-BuLi, 2.) Cl3CCCl3 / 1.) ether, pentane, -78 deg C, 20 min, 0 deg C, 1 h, 2.) ether, pentane, -78 deg C to rt 4: benzene / Ambient temperature 5: 3.46 g / TBAF / tetrahydrofuran / 1 h 6: 99 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C 7: 52 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature; other solvent, reagent, temperature, reaction time 8: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time 9: O2, salcomine / dimethylformamide / 2 h / Ambient temperature 10: methanol / 23 h / Ambient temperature View Scheme

1: 97 percent / NaH / tetrahydrofuran / 0 °C 2: 1.) t-BuLi, 2.) Cl3CCCl3 / 1.) ether, pentane, -78 deg C, 20 min, 0 deg C, 1 h, 2.) ether, pentane, -78 deg C to rt 3: benzene / Ambient temperature 4: 3.46 g / TBAF / tetrahydrofuran / 1 h 5: 99 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C 6: 52 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature; other solvent, reagent, temperature, reaction time 7: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time 8: O2, salcomine / dimethylformamide / 2 h / Ambient temperature 9: methanol / 23 h / Ambient temperature View Scheme

1: O2, salcomine / dimethylformamide / 2 h / Ambient temperature 2: methanol / 23 h / Ambient temperature View Scheme

1: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time 2: O2, salcomine / dimethylformamide / 2 h / Ambient temperature 3: methanol / 23 h / Ambient temperature View Scheme

1: 52 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature; other solvent, reagent, temperature, reaction time 2: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time 3: O2, salcomine / dimethylformamide / 2 h / Ambient temperature 4: methanol / 23 h / Ambient temperature View Scheme

in ethanol 4 h; Heating;

in methanol 23 h; Ambient temperature;