1: 1.) n-BuLI, 2.) / 1.) dioxane, from 5 deg C to 25 deg C, 1.5 h, 2.) dioxane, reflux, 40 h 2: 99 percent / NaHCO3, H2 / 5percent Rh/C / ethyl acetate / 18 h / 760 Torr 3: 87 percent / AG 50W-X4 / CH2Cl2; methanol / 1 h / Ambient temperature 4: 93 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 5: 98 percent / CH2Cl2 / 18 h / Ambient temperature 6: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 1) BuLi / 1) THF, -78 deg C, 30 min, 2) THF, -78 to 20 deg C then 24 h, RT 2: MeOH, Amberlyst 15H / 1) THF, hexane View Scheme

1: Ethylmagnesium chloride,anhydrous cuprous chloride / THF, reflux, 1h 2: 6 percent / Hydrogen / 5percent Rh/alumina / pentane / 0.75 h / -78 °C View Scheme

(i) MeLi, THF, Et2O, (ii) /BRN= 605308/, (iii) aq. MeOH, TsOH; Multistep reaction;

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 72 percent / HMPA / tetrahydrofuran; hexane / 2 h / 0 - 20 °C 2.1: 63 percent / lithium aluminum hydride / diethyl ether / 3 h / 20 °C View Scheme

1: With n-butyllithium 2: With lithium aluminium tetrahydride in diethyl ether Heating;

1: (i) MeLi, THF, Et2O, (ii) /BRN= 1735836/, (iii) aq. MeOH, TsOH 2: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: 1.) EtMgBr 2: 81 percent / LiAlH4 3: 57 percent / pyridine / CH2Cl2 / 15 h / 20 °C View Scheme

1: 1.) EtMgBr 2: 81 percent / LiAlH4 3: 67 percent / pyridine / CH2Cl2 / 16 h / 20 °C View Scheme

1: 1.) EtMgBr 2: 81 percent / LiAlH4 3: 57 percent / pyridine / CH2Cl2 / 15 h / 20 °C 4: 1.) MgBr2, LiBr / 2.) THF, -15 deg C, 2-3 h View Scheme