1: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature 2: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h 3: LiAlH4 / diethyl ether / 3 h / 0 °C 4: imidazole / dimethylformamide / 1 h / Ambient temperature 5: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h 6: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature 7: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature 8: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature 9: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C 10: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature 11: benzenesulfonyl chloride, pyridine / 15 h / 0 °C 12: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h 13: DCC, DMAP / CH2Cl2; dimethylformamide / 1 h / Ambient temperature 14: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / Ambient temperature 15: CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature 2: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h 3: LiAlH4 / diethyl ether / 3 h / 0 °C 4: imidazole / dimethylformamide / 1 h / Ambient temperature 5: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h 6: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature 7: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature 8: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature 9: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C 10: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature 11: benzenesulfonyl chloride, pyridine / 15 h / 0 °C 12: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h 13: DCC, DMAP / CH2Cl2; dimethylformamide / 1 h / Ambient temperature View Scheme