potassium carbonate; sodium iodide in acetonitrile T=20°C; RefluxInert atmosphere;

potassium carbonate in water; acetonitrile

1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 1.2: 2 h / -78 °C 1.3: -78 °C 2.1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr 3.1: sodium hydroxide; water / ethanol / 3 h / 50 °C 3.2: 20 °C 3.3: pH 1 - 2 4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C 5.1: hydrogen; acetic acid / palladium 10 on activated carbon / ethanol / 20 °C / 760.05 Torr 5.2: pH 10 View Scheme

1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 1.2: 2 h / -78 °C 1.3: -78 °C 2.1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr 3.1: sodium hydroxide; water / ethanol / 3 h / 50 °C 3.2: 20 °C 3.3: pH 1 - 2 4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C View Scheme

1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 1.2: 2 h / -78 °C 1.3: -78 °C 2.1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr 3.1: sodium hydroxide; water / ethanol / 3 h / 50 °C 4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C View Scheme

1: 4-bromo-1-methoxy-2-(3-methoxypropoxy)benzene With isopropylmagnesium chloride in tetrahydrofuran 0.25 h; Inert atmosphereCooling with ice; 2: With n-butyllithium in tetrahydrofuran; hexane 4 h; Inert atmosphere; 3: [(1S,3S)-3-bromomethyl-1-((2S,4S)-4-isopropyl-5-oxofuranidin-2-yl)-4-methylpentyl]-carbamic acid tert-butyl ester With iron (III) acetylacetonate in tetrahydrofuran; hexane T=-20 - 20°C; Inert atmosphere; Solvent;

1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 1.2: 2 h / -78 °C 1.3: -78 °C 2.1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr 3.1: sodium hydroxide; water / ethanol / 3 h / 50 °C View Scheme

1: 4-bromo-1-methoxy-2-(3-methoxypropoxy)benzene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.75 h; Inert atmosphere; 2: N-methoxy-N,3-dimethylbutanamide in tetrahydrofuran; hexane T=-78°C; Inert atmosphere;

1: 4-bromo-1-methoxy-2-(3-methoxypropoxy)benzene With n-butyllithium in tetrahydrofuran; hexane T=-70°C; 2 h; 2: (3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro-furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester in tetrahydrofuran; hexane T=-70 - -50°C; 3: With water; citric acid in tetrahydrofuran; hexane T=0 - 5°C; 0.333333 h;