1: 75 percent AcOH / 1 h / 30 °C 2: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min 3: NaOAc / 0.67 h / 130 °C 4: 1 percent NaOMe / methanol / 1 h / Ambient temperature 5: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C 6: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h 7: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 8: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 9: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 10: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 11: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C 2: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h 3: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 4: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 5: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 6: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 7: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: 1 percent NaOMe / methanol / 1 h / Ambient temperature 2: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C 3: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h 4: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 5: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 6: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 7: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 8: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h 2: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 3: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 4: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 5: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 6: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 2: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 2: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 3: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 2: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 3: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 4: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 5: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 2: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 3: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 4: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 5: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 6: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

1: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 2: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 3: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 4: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme

n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min; Multistep reaction;