1: 96 percent / 125 °C 2: 1.) butyllithium, B(OBu)3, 2.) 30percent H2O2, 3.) (NH4)2SO4 View Scheme

1: permanganate 2: NaOH-solution; copper / 200 °C View Scheme

1.1: toluene / Heating 2.1: dimethylamine-boran complex; acetic acid 3.1: LDA / tetrahydrofuran / -78 - 20 °C 3.2: 17 percent / manganese dioxide View Scheme

1: 51 percent / Br2 / acetic acid / 60 °C 2: 1.) quinoline, pyridine, 2.) aq. K2CO3, n-Bu4NI / 1.) 160 deg C, 2.) CH2Cl2 3: 74 percent / NH4OAc / acetic acid 4: LiAlH4 / tetrahydrofuran / Heating 5: Et3N / CH2Cl2 6: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 7: TFA / CHCl3 View Scheme

nitric acid in acetic acid

1: bromine / acetic acid / 60 °C 2: sodium tetrahydroborate / methanol / -20 - 20 °C 3: triethylamine; p-toluenesulfonyl chloride / acetonitrile / Reflux 4: boron tribromide / dichloromethane / 0 - 20 °C View Scheme

1: 94 percent / NaBH4 / ethanol / 0.5 h / 20 °C 2: 59 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 2 h / 20 °C 3: 17 percent / K2CO3; CuO; pyridine / 6 h / Heating 4: 36 percent / H2 / Pd/C / ethyl acetate / 20 °C / atmospheric pressure 5: 11 mg / BBr3 / CH2Cl2 / 1.5 h / 20 °C View Scheme

sodium cyanoborohydride; zinc(II) iodide in 1,2-dichloro-ethane 20 h; Heating;

boron trifluoride diethyl etherate; sodium cyanoborohydride in tetrahydrofuran 10 h; Heating;

1: 96 percent / sodium hydride (80percent oil) / tetrahydrofuran / 1.5 h / Heating 2: 1.) magnesium turnings, iodine; 2.) iodomethane / 1.) THF, reflux; 2.) THF, reflux, then r.t. 2 h 3: 100 percent / H2 / palladium-on-carbon / ethanol / Ambient temperature 4: 4.6 g / thionyl chloride / 8 h / Heating 5: CH2Cl2 / Ambient temperature 6: 81 percent / tetrahydrofuran / 15 h / Ambient temperature 7: 1.) hydriodic acid; 2.) hydriodic acid / 1.) glacial acetic acid, reflux, 2 h; 2.) acetic acid, reflux, 7 h 8: 1.) potassium carbonate; 2.) pyridine, dimethylaminopyridine / 1.) DMSO, acetone, r.t., 2 h 9: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 10: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C View Scheme