1: With water; lithium hydroxide hydrate in tetrahydrofuran T=20°C; 2: With ammonium chloride in tetrahydrofuran; water; ethyl acetate

water; lithium hydroxide hydrate in tetrahydrofuran T=20°C; 3 h;

1: With water; sodium hydroxide in tetrahydrofuran; methanol T=25 - 35°C; 4 h; 2: With hydrogenchloride in water pH=1 - 2; Product distribution / selectivity;

Amycolatopsis coloradensis VKM Ac-1732 in methanol; aq. phosphate buffer pH=7; Microbiological reaction;

1.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 2.2: 0 - 5 °C 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 3.2: pH 1 - 2 View Scheme

Saccharothrix longispora VKM Ac-1265 in methanol; aq. phosphate buffer pH=7; Microbiological reaction;

1.1: hydrogen / palladium 10 on activated carbon / N,N-dimethyl-formamide / 3 h / 25 - 35 °C / 3102.97 Torr 2.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 4.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 4.3: Cooling 5.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 6.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 6.2: Cooling 7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 8.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 9.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 10.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 11.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 11.2: 0 - 5 °C 12.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 12.2: pH 1 - 2 View Scheme

1.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 2.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 3.2: 0 - 5 °C 4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 4.2: pH 1 - 2 View Scheme

1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 3.3: Cooling 4.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 5.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 5.2: Cooling 6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 7.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 8.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 9.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 10.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 10.2: 0 - 5 °C 11.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 11.2: pH 1 - 2 View Scheme

1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 2.3: Cooling 3.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 4.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 4.2: Cooling 5.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 6.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 7.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 8.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 9.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 9.2: 0 - 5 °C 10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 10.2: pH 1 - 2 View Scheme