10 palladium on carbon; hydrogen in methanol

potassium carbonate in methanol Ambient temperature;

1: NaOMe / methanol 2: 0.87 g / acetic acid; H2 / 10percent Pd/C / methanol; H2O / 760.05 Torr View Scheme

1: tetrabutylammonium hydrogen sulphate (TBAHS), 1 M aq. NaOH / CH2Cl2 / 25 °C 2: ammonium formate / 10percent Pd/C / methanol / 0.08 h / Heating 3: NaOMe / methanol View Scheme

1: tetrabutylammonium hydrogen sulphate (TBAHS), 1 M aq. NaOH / CH2Cl2 / 25 °C 2: ammonium formate / 10percent Pd/C / methanol / 0.08 h / Heating 3: NaOMe / methanol View Scheme

1: 93.5 percent / PBr3, H2O / CH2Cl2 / 10 h / 30 °C 2: 61.3 percent / Ag2O / acetonitrile / 40 °C 3: 98.3 percent / H2 / Pd-C (10percent) / dioxane / 35 °C / 760 Torr 4: 92.3 percent / K2CO3 / methanol / Ambient temperature View Scheme

1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 °C 2: palladium on activated charcoal; sodium tetrahydroborate / dichloromethane; methanol / 0.25 h / 0 °C 3: sodium methylate; methanol / 16 h / 20 °C View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C 2: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 °C 3: palladium on activated charcoal; sodium tetrahydroborate / dichloromethane; methanol / 0.25 h / 0 °C 4: sodium methylate; methanol / 16 h / 20 °C View Scheme

1: benzylamine / tetrahydrofuran / 16 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C 3: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 °C 4: palladium on activated charcoal; sodium tetrahydroborate / dichloromethane; methanol / 0.25 h / 0 °C 5: sodium methylate; methanol / 16 h / 20 °C View Scheme

Agrobacterium sp ABG E358S gomodenate in various solvent(s) 17 h; Enzymatic reaction;