hydrogen; palladium dihydroxide in methanol; water 24 h;

2: H2 / Pd/C / ethanol View Scheme

1: dimethylsulfoxide; dimethylformamide / 36 h / Ambient temperature 2: LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 2 h 3: POCl3, Et3N / CHCl3 / 0.5 h / Ambient temperature 4: pyridine / 1.) CHCl3, RT, 16 h, 2.) 30 min 5: 100 percent / H2 / 20percent Pd(OH)2/C / methanol; H2O / 24 h View Scheme

1: KOtBu / tetrahydrofuran / 1) r.t., 1 h, 2) reflux, 3 h 2: BF3 / CH2Cl2; methanol / 2 h / 0 °C 4: H2 / Pd/C / ethanol View Scheme

1: BF3 / CH2Cl2; methanol / 2 h / 0 °C 3: H2 / Pd/C / ethanol View Scheme

1: 74 percent / KOtBu 2: 80 percent / Et3N / tetrahydrofuran / 20 h / Ambient temperature 3: KOtBu / tetrahydrofuran / 1) r.t., 1 h, 2) reflux, 3 h 4: BF3 / CH2Cl2; methanol / 2 h / 0 °C 6: H2 / Pd/C / ethanol View Scheme