1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere 2.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve 2.2: 0.67 h / 5 °C 3.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4.1: ozone / methanol / 0.5 h / -78 °C 4.2: 0 - 20 °C View Scheme

1.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve 1.2: 0.67 h / 5 °C 2.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 3.1: ozone / methanol / 0.5 h / -78 °C 3.2: 0 - 20 °C View Scheme

1.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 2.1: ozone / methanol / 0.5 h / -78 °C 2.2: 0 - 20 °C View Scheme

1.1: lipase AK Amano 20 / 9.5 h / 20 °C / Inert atmosphere; Enzymatic reaction 2.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3.1: methanol; potassium carbonate / 3 h / 20 °C 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 5.2: -78 - 20 °C / Inert atmosphere 6.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere 7.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere 9.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve 9.2: 0.67 h / 5 °C 10.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 11.1: ozone / methanol / 0.5 h / -78 °C 11.2: 0 - 20 °C View Scheme

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: methanol; potassium carbonate / 3 h / 20 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere 4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere 8.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve 8.2: 0.67 h / 5 °C 9.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 10.1: ozone / methanol / 0.5 h / -78 °C 10.2: 0 - 20 °C View Scheme

hydrogenchloride in acetone

Na[AlH2(OMe)2] in tetrahydrofuran; toluene 12 h; Heating; Product distribution; Further Variations:Reagents;

acetic acid T=25°C; 18 h; Var.: methanol, reflux. Stable under basic conditions; Product distribution;

sodium hydride; tetra-(n-butyl)ammonium iodide in tetrahydrofuran; Petroleum ether 3 h;

1: With sodium hypochlorite; tetrabutylammomium bromide; sodium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate in dichloromethane T=0 - 20°C; 1 h; 2: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene in tetrahydrofuran; water; tert-butyl alcohol T=20°C; Further stages.;