1: 1) 9-borabicyclo(3.3.1)nonane; 2) potassium 2,6-di-t-butyl-4-methyl-phenoxide / 1) room temperature; 2) 0 deg C, 1 h 2: 93 percent / diisobutylaluminum hydride 3: 91 percent / NaH / 4 h / Heating 4: 95 percent / hydrogen / 5percent Pd/charcoal / 15 h / Ambient temperature 5: 99 percent / 2 h / Heating View Scheme

1: 100 percent / imidazole / dimethylformamide / Ambient temperature 2: 75 percent / BF3*OEt2 / CH2Cl2 / 0.17 h / Ambient temperature 3: 86 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature 4: 96 percent / diethyl ether / 1 h / Ambient temperature 5: 83 percent / pyridinium dichromate, 4A MS / CH2Cl2; dimethylformamide / 2 h / Ambient temperature 6: 96 percent / CH(OEt)3, TsOH*H2O / CH2Cl2 / 96 h / Ambient temperature 7: 95 percent / TBAF / tetrahydrofuran / 10 h / Ambient temperature 8: 96 percent / imidazole / dimethylformamide / Ambient temperature 9: 41 percent / OsO4, pyridine / diethyl ether / 3 h / -20 - 20 °C 10: 78 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 - 20 °C 11: 93 percent / CeCl3*7H2O, NaBH4 / tetrahydrofuran / 3 h / 0 °C 12: 69 percent / 4A MS, TMSOTf / CH2Cl2 / 0.33 h / -20 °C 13: 79 percent / Pd(MeCN)2Cl2 / acetone; H2O / Ambient temperature View Scheme