1: 98 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -50 deg C 3: DIBAL / tetrahydrofuran; toluene / 2 h / -78 °C 4: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min 5: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 7: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 8: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 9: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 10: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 11: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 12: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 3: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 4: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 5: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 6: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 7: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 8: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

2: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 3: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 4: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 5: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 6: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 7: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

2: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 3: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 4: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 5: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 6: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 7: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -50 deg C 2: DIBAL / tetrahydrofuran; toluene / 2 h / -78 °C 3: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min 4: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 6: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 7: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 8: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 9: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 10: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 11: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 3: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 4: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 5: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 6: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 7: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 8: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: DIBAL / tetrahydrofuran; toluene / 2 h / -78 °C 2: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min 3: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 5: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 6: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 7: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 8: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 9: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 10: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 2: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 3: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 4: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 5: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 6: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min 2: 1) Me3OBF4, 2) aq.Na2CO3 / 1) CH2Cl2, r.t., 2 h, 2) 6 h 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

hydrogen; boric acid; palladium on activated charcoal; nickel 1.) MeOH-H2O 5-1, 3.5 h, room temp., 2.) MeOH, 40 min, room temp.; Multistep reaction;