1: NaBH4 / diethyl ether; methanol / 1 h 2: 19 percent Chromat. / BF3-etherate / CH2Cl2 / 0.5 h 3: 79 percent / H2 / PtO2 / ethanol / 10 h / 760 Torr / Ambient temperature 4: 48 percent / RuO2*xH2O/NaIO4 / CCl4 / 2.5 h / 20 °C 5: 5 mg / K2CO3 / m-xylene / 5 h / Heating 6: diisopropylamine/n-BuLi / hexane; tetrahydrofuran / 1.5 h 7: NaIO4 / CH2Cl2; H2O / 0.58 h / Ambient temperature 8: toluene / 5 h / Heating 9: 77 percent / DIBAL / tetrahydrofuran / 20 h View Scheme

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

1: NaBH4 / diethyl ether; methanol / 1 h 2: 79 percent / 1.) 98percent HCOOH; 2.) aq. KOH / 2.5 h / 20 °C 3: 231 mg / pyridine / 30 °C 4: 78 percent / LiAlH4 / diethyl ether / 0.5 h / Heating View Scheme

1: n-BuLi / tetrahydrofuran / 5 h / -78 °C 2: p-toluenesulfonic acid / CH2Cl2 3: MeOK / cyclohexane / 2 h / 38 °C 4: Et3N / hexane View Scheme

1: NaBH4 / diethyl ether; methanol / 1 h 2: 79 percent / 1.) 98percent HCOOH; 2.) aq. KOH / 2.5 h / 20 °C View Scheme