1: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 3: concd. NH4OH / acetone / 1.5 h 4: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 5: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 6: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 3: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 5: concd. NH4OH / acetone / 1.5 h 6: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 7: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 8: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h 2: LiAlH4 / diethyl ether / 3 h / Ambient temperature 3: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 4: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 6: concd. NH4OH / acetone / 1.5 h 7: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 8: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 9: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

2: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 3: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h 4: LiAlH4 / diethyl ether / 3 h / Ambient temperature 5: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 6: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 8: concd. NH4OH / acetone / 1.5 h 9: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 10: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 11: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: 93 percent / KOH / diethyl ether / 6 h 2: 81 percent / NaI / acetone / 24 h / Ambient temperature 3: 75 percent / tetrahydrofuran / 24 h / Ambient temperature 4: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 5: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: 81 percent / NaI / acetone / 24 h / Ambient temperature 2: 75 percent / tetrahydrofuran / 24 h / Ambient temperature 3: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 4: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: 75 percent / tetrahydrofuran / 24 h / Ambient temperature 2: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 3: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 2: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 4: concd. NH4OH / acetone / 1.5 h 5: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 6: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 7: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

2: concd. NH4OH / acetone / 1.5 h 3: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 4: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 5: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 2: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h 3: LiAlH4 / diethyl ether / 3 h / Ambient temperature 4: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 7: concd. NH4OH / acetone / 1.5 h 8: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 9: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 10: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme