1: 92 percent / Na2Cr2O7, H2SO4 / diethyl ether; H2O / 3 h 2: 1) NaH / 1) DMSO, 2 h, 80 deg C, 2) DMSO, 2 h, 50 deg C 3: 92 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 95 percent / pyridine / 24 h / Ambient temperature 5: 72 percent / LiBr / tetrahydrofuran / 36 h / Heating View Scheme

1: chromic acid 2: 93 percent / p-toluene sulfonic acid 3: 1.) Ph3CLi / 1) cooling (ice-bath), 45 min, THF, hexane; 2) THF, hexane, cooling (ice-bath), 90 min View Scheme

pyridine; sodium; benzene Erwaermen des Reaktionsprodukts mit aethanol. KOH;

1H-imidazole in DMF (N,N-dimethyl-formamide) T=35°C; 12 h;

triethylamine in dichloromethane T=0 - 20°C; 12 h; Molecular sieveInert atmosphere;

in N-methyl-acetamide; diethyl ether

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 2.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 2 h / 70 °C 2.2: pH 3 - 4 3.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 60 °C 3.2: -78 - 20 °C 4.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 115 °C 5.1: isobutyramide / 20 °C 6.1: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 20 °C View Scheme

1: CrO3, H2SO4 / acetone; H2O 2: Br2 / diethyl ether View Scheme

hydrogenchloride Erwaermen des Reaktionsprodukts mit SOCl2;

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 2.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 2 h / 70 °C 2.2: pH 3 - 4 3.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 60 °C 3.2: -78 - 20 °C 4.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 115 °C 5.1: isobutyramide / 20 °C 6.1: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 20 °C 7.1: pyridinium chlorochromate / dichloromethane / 18 h / 20 °C View Scheme