1: 85 percent / KMnO4, K2CO3 / H2O / 1) 0 deg C, 30 min., 2) 50 deg C, 2 h 2: 63 percent / HCl, HOAc / methanol View Scheme

1: 1.) aq. K2CO3, 30percent aq. H2O2 / 1.) 20 deg C, overnight, 2.) CH3CN, reflux, 24 h 2: pyridine, DMAP / CH2Cl2 3: LiCl / dimethylformamide 4: H2, Et3N / 10percent Pd/C / methanol 5: DIBAL-H / toluene / -78 °C View Scheme