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

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