1: 1.) sodiobis(trimethylsilyl)amide / 1.) THF, 50-55 deg C, 2.) -78 deg C; 20 deg C 2: 95 percent / HCl / H2O; acetone / 20 °C 3: 87 percent / LiAlH4 / diethyl ether / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H2 / Pd(OH)2/C / methanol 3.1: PCC; NaOAc; molecular sieves / CH2Cl2 3.2: 76 percent / Et3N / CH2Cl2 4.1: 87 percent / NaBH4 / CeCl3 / methanol 5.1: 83 percent / (+)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH2Cl2 / -20 °C 6.1: DBU / CH2Cl2 / 1.5 h / 0 °C 6.2: 74 percent / Et2AlCl / CH2Cl2 / 0 - 20 °C 7.1: 1H-tetrazole / CH2Cl2; acetonitrile / 6 h 7.2: 78 percent / t-BuOOH / 20 °C 8.1: 81 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme

(i) K, HMPT, (ii) /BRN= 2358373/; Multistep reaction;

sodium hexamethyldisilazane in tetrahydrofuran -78 deg C, 1 h then 25 deg C 12 h;

HMDS in tetrahydrofuran -78 deg C, 1 h then 25 deg C, 12 h;

sodium hexamethyldisilazane; pyridinium chlorochromate 1) methylene chloride 20-25 deg C 2) THF 20 deg C 30 min, reflux 1 h 3) -78 deg C 1 h, 25 deg C 12 h; Yield given. Multistep reaction;

HMDS; pyridinium chlorochromate 1) methylene chloride 20-25 deg C 2) THF 20 deg C 30 min, reflux 1 h, 3) -78 deg C, 25 deg C 12 h; Yield given. Multistep reaction;

sodium hexamethyldisilazane 1) THF 20 deg C, 30 min, 1 h reflux 2) -78 deg C 1 h, 20-25 deg C 12 h; Yield given. Multistep reaction;

sodium hexamethyldisilazane 1) THF 20 deg C 30 min, 1 h reflux 2) -78 deg C 1 h, 29-25 deg C 12 h; Yield given. Multistep reaction;