1: 1.) N-methylmorpholine N-oxide, osmium tetroxide; 2.) p-toluenesulfonic acid / 1.) t-butyl alcoho-THF-water (10.10:1), r.t., 18 h; 2.) CHCl3, r.t., 1 h 2: 458 mg / 10 N NaOH / methanol / 3 h / Heating View Scheme

1: 1.) N-methylmorpholine N-oxide, osmium tetroxide; 2.) p-toluenesulfonic acid / 1.) t-butyl alcoho-THF-water (10.10:1), r.t., 18 h; 2.) CHCl3, r.t., 1 h 2: trifluoroperacetic acid, Na2HPO4 (powdered) / CH2Cl2 / 1.) 5 deg C, 1 h; 2.) 30 deg C, 3 h 3: 1.79 g / 10 N NaOH / methanol / 3 h / Heating View Scheme