1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 2: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 3: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 4: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 6: H2 View Scheme

1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 2: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 3: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 4: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme

1: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 2: (+)-diisopinocamphenylchloroborane / tetrahydrofuran / 20 h / -30 °C 3: 100 percent / Et3N / CH2Cl2 / 0.08 h / 0 °C 4: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5: B(C6H11)2H / tetrahydrofuran 6: 94 percent / HCOOH / H2O / 3 h / 80 °C 7: 83 percent / CuI; Ph3P; K2CO3 / Pd/C / 1,2-dimethoxy-ethane / 16 h / Heating 8: 92 percent / NaH / toluene / 2 h / Heating View Scheme