1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide 4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 5: 82 percent / TEA, DMAP / CH2Cl2 6: Dess-Martin reagent, t-BuOH / CH2Cl2 7: Zn, TiCl4 / tetrahydrofuran; CH2Cl2 8: 92 percent / aq. HCl / tetrahydrofuran; methanol / 55 °C 9: 89 percent / BCl3 / CH2Cl2 / -78 °C View Scheme

1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide 4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C View Scheme

1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide 4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 5: 82 percent / TEA, DMAP / CH2Cl2 6: Dess-Martin reagent, t-BuOH / CH2Cl2 7: Zn, TiCl4 / tetrahydrofuran; CH2Cl2 View Scheme

1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide 4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 5: 82 percent / TEA, DMAP / CH2Cl2 View Scheme

1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C 3.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C 3.2: hydroxylamine-O-sulfonic acid / tetrahydrofuran / 3 h / 70 °C View Scheme

1: With (Ipc)2BH in tetrahydrofuran T=-20 - -18°C; 2: With dihydrogen peroxide; sodium hydroxide