1: With water; sodium hydrogencarbonate T=0°C; 0.25 h; 2: With sodium tetrahydroborate T=0 - 20°C; 5 h; 3: With hydrogenchloride in water T=0°C; pH=2 - 3; Product distribution / selectivity;

1.1: sodium hydrogencarbonate; water / 0.25 h / 0 °C 1.2: 5 h / 0 - 20 °C 1.3: 0 °C / pH 2 - 3 2.1: acetic anhydride; pyridine / toluene / 20 °C 3.1: Reduced nicotinamide-adenine dinucleotide; NADPH; Citrobacter sp. N-ethylmaleimide reductase / dimethyl sulfoxide / 22 h / 30 °C / pH 7 / Enzymatic reaction; Aqueous phosphate buffer 4.1: potassium hydroxide; water / 6 h / 25 °C 5.1: hydrogen / Raney Nickel / water / 30 °C 6.1: acetic acid / ethanol / 35 °C / pH 7.5 View Scheme

ammonium acetate in toluene Reflux;

1: water / 108 h / 20 °C 2: alcohol dehydrogenase from Lactobacillus brevis; 12-oxophytodienoic acid reductase isoenzyme OPR1-wt from Lycopersicon esculentum / isopropyl alcohol; aq. phosphate buffer / 22 h / 30 °C / pH 7.5 / |Enzymatic reaction 3: palladium on carbon / isopropyl alcohol / 4 h / 30 °C View Scheme