1: 90 percent / H2 / P-2 nickel 2: mesylation 3: 76 percent / NaI / acetone 4: 66 percent / ethylmagnesium bromide / CuCl 5: 80 percent / LiAlH4 6: mesylation 7: LiAlH4 8: 79 percent / acetylation View Scheme

1: H2 / Lindlar catalyst / ethanol / 0 °C 2: MnO2 / toluene 3: t-BuOK / tetrahydrofuran 4: p-TsOH / methanol 5: pyridine View Scheme

1: 99 percent / pyridine / 3 h / Ambient temperature 2: 1.) Jones reagent, 2.) AcCl / 1.) acetone, 0 deg C, 2.) r.t., 2 h View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 12 h;

1: pyridinium chlorochromate (PCC) / CH2Cl2 / 1 h 2: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h 3: LAH, ethanol / diethyl ether / 0.5 h / 0 °C 4: H2 / Lindlar's catalyst / hexane; ethanol 5: TEA / CH2Cl2 / 4 h / 0 °C 6: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h 7: 82 percent / PTS / methanol / Ambient temperature View Scheme

1: 5.8 g / LiAlH4 / diethyl ether / 16 h / Ambient temperature 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C 45 min, 2.) CH2Cl2, from -78 deg C to RT 3: 1.) BuLi / 1.) hexane, THF, from -30 deg C to RT, 2.) hexane, THF, from -30 deg C to RT 4: PTSA / methanol / Ambient temperature View Scheme