1: 85.1 percent / BH3*SMe2 / tetrahydrofuran / 3 h / 20 °C 2: 77.7 percent / Et3N / CH2Cl2 / 20 h / 22 °C View Scheme

toluene-4-sulfonic acid in methanol 5 h; Ambient temperature;

1: Dibal-H / CH2Cl2; diethyl ether 2: 74 percent / pyridine 3: 91 percent / 1.5 h / 190 °C / 0.5 Torr / Heating 4: 1.) t-BuLi, 2.) BF3*OEt2 / 1.) THF, pentane, -78 deg C, 1 h, 2.) THF, pentane, ether, -78 deg C, 30 min, then -10 deg C, 30 min 5: 35 percent / pyridinium p-toluenesulfonate / benzene / Ambient temperature View Scheme

1.1: LiHMDS / -78 °C 1.2: MoOPH / 0.5 h / -25 °C 2.1: 85 percent / pyridine / 0 - 20 °C 3.1: tetrahydrofuran; toluene; pyridine / -40 °C 4.1: H2 / Pd on CaCO3 / tetrahydrofuran / 1500.12 Torr 5.1: K2CO3 / methanol 6.1: DEAD; PPh3 / tetrahydrofuran / 0 °C 7.1: aq. K2CO3 / methanol 8.1: 70 percent / NaOAc / 60 °C 9.1: FeCl3*6H2O / CH2Cl2 / 0.33 h / 20 °C 10.1: pyridine / -20 °C 11.1: NaI / butan-2-one / 80 °C 12.1: 72 percent / aq. K2CO3 / methanol 13.1: 92 percent / ethanol / Heating View Scheme

potassium hydroxide; triphenylphosphine; diethylazodicarboxylate 1.) MeOH, 60 deg C, 2 h; 2.) THF, room temp., 24 h; Yield given. Multistep reaction;

1: lithium diisopropylamide (LDA) / tetrahydrofuran / -78 °C 2: NaIO4, 18-crown-6 / H2O; ethyl acetate / 60 °C View Scheme

1: 1.) LDA / 1.) THF, -78 degC, 35 min; 2.) THF, -78 degC, 1.5 h 2: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 3: 1.) n-BuLi / 1.) n-hexane, THF, -78 degC, 30 min; 2.) THF, -78 degC, 2 h View Scheme

1: 1.) LDA / 1.) THF, -78 degC, 35 min; 2.) THF, -78 degC, 1.5 h 2: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 3: 1.) n-BuLi / 1.) n-hexane, THF, -78 degC, 30 min; 2.) THF, -78 degC, 2 h 4: 65 percent / Raney-Ni / ethanol / 5 h / Heating View Scheme

1: 1.) LDA / 1.) THF, -78 degC, 35 min; 2.) THF, -78 degC, 1.5 h 2: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 3: 1.) n-BuLi 4: 28 percent / Raney-Ni / ethanol / 12 h / Heating 5: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme