1: 19 percent Chromat. / BF3-etherate / CH2Cl2 / 0.5 h 2: 79 percent / H2 / PtO2 / ethanol / 10 h / 760 Torr / Ambient temperature 3: 48 percent / RuO2*xH2O/NaIO4 / CCl4 / 2.5 h / 20 °C 4: 5 mg / K2CO3 / m-xylene / 5 h / Heating 5: diisopropylamine/n-BuLi / hexane; tetrahydrofuran / 1.5 h 6: NaIO4 / CH2Cl2; H2O / 0.58 h / Ambient temperature 7: toluene / 5 h / Heating 8: 77 percent / DIBAL / tetrahydrofuran / 20 h View Scheme

1: PDC / CH2Cl2 / 10 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h 3: p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature 4: MeOK / cyclohexane / 2 h / 38 °C View Scheme

1: 79 percent / 1.) 98percent HCOOH; 2.) aq. KOH / 2.5 h / 20 °C 2: 231 mg / pyridine / 30 °C 3: 78 percent / LiAlH4 / diethyl ether / 0.5 h / Heating View Scheme

potassium hydroxide; formic acid T=20°C; 2.5 h;

1: PBr3 / diethyl ether / 0.33 h / -25 °C 2: BuLi, N,N'-dimethyl-N,N'-propyleneurea / hexane; tetrahydrofuran / 1.) -78 deg C, 1 h; 2.) -50 deg C, 1 h 3: 75.5 percent / KOH / diethyl ether; methanol / 1 h / Ambient temperature 4: 52 percent / Na, dibenzo<18>crown-6 / liquid ammonia; tetrahydrofuran / 0.03 h View Scheme