tetrabutyl ammonium fluoride in tetrahydrofuran T=0°C; 6 h; Inert atmosphere;

palladium 10 on activated carbon; hydrogen; triethylamine in ethyl acetate 4 h;

1: 98 percent / H2, NaOH / 10percent Pd/C / H2O / 12 h / 22501.8 Torr 2: 98 percent / conc.H2SO4 / Heating 3: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C 4: 95 percent / LiAlH4 / diethyl ether / 0 °C 5: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 6: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 8: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 9: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 10: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 11: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 12: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 13: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 2: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 4: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 5: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 6: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 7: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 8: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 9: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 75 percent / NaH / 1,2-dimethoxy-ethane / 24 h / Heating 2: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature 3: 76 percent / pyridine / 16 h / 5 °C 4: 86 percent / NaI / acetone / 21 h / Ambient temperature 6: 1.) B(OH)3, H2, 2.) H2 / 1.) Raney Ni, 2.) 10 percent Pd/C / 1.) MeOH-H2O 5-1, 3.5 h, room temp., 2.) MeOH, 40 min, room temp. View Scheme

1: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature 2: 76 percent / pyridine / 16 h / 5 °C 3: 86 percent / NaI / acetone / 21 h / Ambient temperature 5: 1.) B(OH)3, H2, 2.) H2 / 1.) Raney Ni, 2.) 10 percent Pd/C / 1.) MeOH-H2O 5-1, 3.5 h, room temp., 2.) MeOH, 40 min, room temp. View Scheme

1: H2SO4 2: 78 percent / NaH, Bu4NI / tetrahydrofuran / 13 h / Ambient temperature 3: 80 percent / LDA / tetrahydrofuran / 1.) from 0 deg C to r.t.; 2.) reflux, 30 min 4: 81 percent / TMEDA, NaH / dimethylsulfoxide / 0.75 h 5: catecholborane / tetrahydrofuran / 4.5 h / -23 °C 6: Raney-Ni / ethanol / 0.5 h / Ambient temperature View Scheme

1: 80 percent / LDA / tetrahydrofuran / 1.) from 0 deg C to r.t.; 2.) reflux, 30 min 2: 81 percent / TMEDA, NaH / dimethylsulfoxide / 0.75 h 3: catecholborane / tetrahydrofuran / 4.5 h / -23 °C 4: Raney-Ni / ethanol / 0.5 h / Ambient temperature View Scheme

1: 78 percent / NaH, Bu4NI / tetrahydrofuran / 13 h / Ambient temperature 2: 80 percent / LDA / tetrahydrofuran / 1.) from 0 deg C to r.t.; 2.) reflux, 30 min 3: 81 percent / TMEDA, NaH / dimethylsulfoxide / 0.75 h 4: catecholborane / tetrahydrofuran / 4.5 h / -23 °C 5: Raney-Ni / ethanol / 0.5 h / Ambient temperature View Scheme

1: 99 percent / methanol / Heating 2: 98 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -50 deg C 4: DIBAL / tetrahydrofuran; toluene / 2 h / -78 °C 5: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min 6: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 8: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 9: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 10: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 11: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 12: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 13: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme