1: 100 percent / KOH / methanol / 6 h / Heating View Scheme

1: 1.10 g / NaOEt / ethanol / Heating 2: 420 mg / H2 / PtO2 / ethyl acetate View Scheme

1: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 2: H2 / Pd/C / acetone 3: 5percent aq. NaOH / methanol 4: 1.) Et3N / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, 30 min 5: CH2Cl2 / 1 h View Scheme

1: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 2: H2 / Pd/C / acetone 3: 5percent aq. NaOH / methanol View Scheme

1: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 2: 99 percent / H2 / Pd/C / methanol / 3 h / 1913.4 Torr 3: 96 percent / LiAlH4 / tetrahydrofuran / 1 h / 21 - 29 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 4 h, 2.) CH2Cl2, -65 deg C to -10 deg C, overnight View Scheme

1: 100 percent / KOH / methanol / 6 h / Heating 2: 91 percent / B(OH)3 / toluene / 16 h / Heating View Scheme

1: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 2: 95 percent / PhSH, air / 0.33 h / 95 - 100 °C 3: LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 1 h, 2.) CH2Cl2, -60 deg C 30 min 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 to -20 deg C, 4 h 6: 90 percent / KOH / ethanol; H2O / Ambient temperature 7: (COCl)2 / benzene / 1 h / Heating 8: Et3N / diethyl ether / -5 - 20 °C View Scheme