1: 1.) NaN(SiCH3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, b) r.t., 15 h 2: 97 percent / H2 / 10percent Pd/C / ethyl acetate 3: 95 percent / NaOH / methanol / 20 h / Heating View Scheme

1: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 2: diethyl ether 3: 100 percent / H2 / 10percent Pd/C / ethyl acetate 4: 78 percent / KOH / methanol / 24 h / Heating View Scheme

1: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 2: diethyl ether 3: 97 percent / H2 / 10percent Pd/C / ethyl acetate 4: 90 percent / NaOMe / methanol / Ambient temperature 5: 80 percent / pyridinium chlorochromate / CH2Cl2 / warming with a H2O bath 6: 1.) NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) -20 deg C , 1 h, b) r.t., 15 h 7: TsOH / methanol 8: 93 percent / NaOH / methanol / 27 h / Heating View Scheme