1: tetrahydrofuran / 2 h / 20 °C 2: Et3SiH; boron trifluoride etherate / CH2Cl2 / 4 h / 0 °C 3: Na/Hg; sodium phosphate / methanol / 2 h / 20 °C View Scheme

1: 1.) LHMDS / 1.) THF, from -78 deg C to 0 deg C, 2.) THF, -78 deg C 2: 83 percent / n-Bu4NOTf, aq. K2CO3, 14 percent Pd(OAc)2 / dimethylformamide / 14 h / 55 °C 3: 2,6-lutidine / CH2Cl2 / 0.17 h / Ambient temperature 4: MeOH / CH2Cl2 / 0.25 h / Ambient temperature 5: Et3N / CH2Cl2 / 3 h 6: pyridine*HF / 2 h / Ambient temperature 7: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C 8: 63 percent / KF, KHCO3, 30 percent aq. H2O2 / tetrahydrofuran; methanol / 1.5 h / Heating 9: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 10: AIBN, tributyltin hydride / benzene / 1 h / Heating 11: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

1: tetrahydrofuran / 2 h / 20 °C 2: Et3SiH; boron trifluoride etherate / CH2Cl2 / 4 h / 0 °C 3: Na/Hg; sodium phosphate / methanol / 2 h / 20 °C View Scheme

1: tetrahydrofuran / 2 h / 20 °C 2: Et3SiH; boron trifluoride etherate / CH2Cl2 / 4 h / 0 °C 3: Na/Hg; sodium phosphate / methanol / 2 h / 20 °C View Scheme

1: tetrahydrofuran / 2 h / 20 °C 2: Et3SiH; boron trifluoride etherate / CH2Cl2 / 4 h / 0 °C 3: Na/Hg; sodium phosphate / methanol / 2 h / 20 °C 4: sodium cyanoborohydride / tetrahydrofuran; methanol / 18 h / 20 °C View Scheme