1: 96 percent / sodium bicarbonate / CH2Cl2 / 72 h / 30 °C 2: 92 percent / zinc powder / tetrahydrofuran / 3 h / Heating 3: 101 percent / sodium hydroxide / methanol / 48 h 4: 89 percent / CH3CO3H, Na2CO3, Na2WO4 / methanol; H2O 5: 1) sodium methoxide, 2) sodium borohydride / 1) MeOH, -30 degC, 20min, 2) 25 degC, 6h 6: 84 percent / paraformaldehyde, boron trifluoride etherate / H2O; acetone / 120 h / Ambient temperature View Scheme

1: 96 percent / sodium bicarbonate / CH2Cl2 / 72 h / 30 °C 2: 92 percent / zinc powder / tetrahydrofuran / 3 h / Heating 3: 8 percent / 30percent H2O2, Potassium carbonate / methanol; acetonitrile; H2O / 5 h / 0 °C 4: 82 percent / NaBH4, NaOMe / methanol / 0.5 h 5: 11 percent / paraformaldehyde, BF3*Et2O / acetone; H2O / 120 h / Ambient temperature View Scheme

1: 96 percent / sodium bicarbonate / CH2Cl2 / 72 h / 30 °C 2: 92 percent / zinc powder / tetrahydrofuran / 3 h / Heating 3: 8 percent / 30percent H2O2, Potassium carbonate / methanol; acetonitrile; H2O / 5 h / 0 °C 4: 82 percent / NaBH4, NaOMe / methanol / 0.5 h 5: 83 percent / paraformaldehyde, BF3*Et2O / acetone; H2O / 120 h / Ambient temperature View Scheme

1: 96 percent / sodium bicarbonate / CH2Cl2 / 72 h / 30 °C 2: 92 percent / zinc powder / tetrahydrofuran / 3 h / Heating 3: 101 percent / sodium hydroxide / methanol / 48 h 4: 89 percent / CH3CO3H, Na2CO3, Na2WO4 / methanol; H2O 5: 1) sodium methoxide, 2) sodium borohydride / 1) MeOH, -30 degC, 20min, 2) 25 degC, 6h 6: 11 percent / paraformaldehyde, boron trifluoride etherate / H2O; acetone / 120 h / Ambient temperature View Scheme

Yield given. Multistep reaction. Yields of byproduct given;

1.) THF, -78 deg C, 2.) -40 deg C -> 0 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction. Yields of byproduct given;