sodium hydroxide; sodium tetrahydroborate; 2-methyl-but-2-ene; boron trifluoride; dihydrogen peroxide 1.) THF, room temp., 3 h.; 2.) 50 deg C, 1.5 h; Multistep reaction;

trifluorormethanesulfonic acid; water T=90°C; 1 h; Ionic liquid;

1.1: O3 / CH2Cl2 1.2: 85 percent / Me2S / CH2Cl2 / -78 °C 2.1: trifluoromethanesulfonic acid; triethylborane; diisopropylethylamine / hexane; CH2Cl2 / 0.5 h / 0 °C 2.2: 85 percent / CH2Cl2; hexane / 3 h / -78 - 0 °C 3.1: 92 percent / aq. H2O2; LiOH / tetrahydrofuran / 1 h / 0 °C 4.1: 77 percent / i-PrOTMS; TMSOTf / CH2Cl2 / -78 °C 5.1: 85 percent / tetrahydrofuran / 24 h / Heating 6.1: 85 percent / Me2AlCl / CH2Cl2 / 0.17 h / -78 °C 7.1: LHMDS / tetrahydrofuran; hexane / 1.5 h / -78 - -10 °C 7.2: 70 percent / tetrahydrofuran; hexane / 3 h / -20 - 0 °C 8.1: 81 percent / NaBH4 / ethanol / 2.5 h / -78 °C 9.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / -10 °C 10.1: n-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C 10.2: BF3*Et2O / tetrahydrofuran; pentane / 3 h / -78 °C 11.1: 57 percent / second generation Grubbs' catalyst / CH2Cl2 / 48 h / 50 - 55 °C 12.1: 89 percent / 2,6-lutidine; DMAP / pyridine / 1 h / 0 - 20 °C 13.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 14.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 15.1: 84 percent / BnNMe3OH / methanol; tetrahydrofuran / 1 h / 0 °C 16.1: n-BuLi; WCl6 / tetrahydrofuran; hexane / 0 - 20 °C 17.1: 12 mg / pyridinum p-toluenesulfonate / methanol / 6 h / 0 °C 18.1: 69 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0 - 20 °C 19.1: 40 percent / aq. HF / acetonitrile / 0 - 20 °C View Scheme

T=100°C; Behandeln des Reaktionsprodukts mit Trimethylamin;

1: H2SO4 2: PdCl2, CuCl2 / dimethylformamide 3: NaBH4 / ethanol View Scheme

methanesulfonic acid; molybdovanadophosphate; oxygen; hydroquinone; palladium diacetate; sodium chloride in ethanol T=60°C; Wacker-type oxidation; 5 h;

in methanol

Sn(IV) triflate T=60°C; 24 h;

sulfuric acid

manganese triacetate in 1,4-dioxane 12 h; Heating;