1: 1.) Mg / 1.) ether, 0-5 deg C; 2.) 4 h, r.t., ether 2: 71 percent / 1.) 50 percent NaH / 1.) DMSO, oil, r.t., 30 min.; 2.) DMSO, THF, r.t., 4 h 3: 73 percent / 70 percent t-butylhydroperoxide, Et4NOAc*4H2O / OsO4 / acetone 4: 94 percent / p-TsOH / benzene / 1 h / Heating 5: imidazole / dimethylformamide / 6 h / Ambient temperature 6: 1.) 50 percent NaH, ethyl oxalate; 2.) K2CO3 / 1.) oil, THF, EtOH, 4 h, r.t.; 2.) oil, THF, H2O, 1.5 h, 0 deg C 7: 79.8 percent / acetic acid; tetrahydrofuran; H2O / 72 h / Ambient temperature View Scheme

1: 1.) Mg / 1.) ether, 0-5 deg C; 2.) 4 h, r.t., ether 2: 71 percent / 1.) 50 percent NaH / 1.) DMSO, oil, r.t., 30 min.; 2.) DMSO, THF, r.t., 4 h 3: 73 percent / 70 percent t-butylhydroperoxide, Et4NOAc*4H2O / OsO4 / acetone 4: 94 percent / p-TsOH / benzene / 1 h / Heating 5: imidazole / dimethylformamide / 6 h / Ambient temperature 6: 1.) 50 percent NaH, ethyl oxalate; 2.) K2CO3 / 1.) oil, THF, EtOH, 4 h, r.t.; 2.) oil, THF, H2O, 1.5 h, 0 deg C 7: 79.8 percent / acetic acid; tetrahydrofuran; H2O / 72 h / Ambient temperature View Scheme

1: 71 percent / 1.) 50 percent NaH / 1.) DMSO, oil, r.t., 30 min.; 2.) DMSO, THF, r.t., 4 h 2: 73 percent / 70 percent t-butylhydroperoxide, Et4NOAc*4H2O / OsO4 / acetone 3: 94 percent / p-TsOH / benzene / 1 h / Heating 4: imidazole / dimethylformamide / 6 h / Ambient temperature 5: 1.) 50 percent NaH, ethyl oxalate; 2.) K2CO3 / 1.) oil, THF, EtOH, 4 h, r.t.; 2.) oil, THF, H2O, 1.5 h, 0 deg C 6: 79.8 percent / acetic acid; tetrahydrofuran; H2O / 72 h / Ambient temperature View Scheme

1: 73 percent / 70 percent t-butylhydroperoxide, Et4NOAc*4H2O / OsO4 / acetone 2: 94 percent / p-TsOH / benzene / 1 h / Heating 3: imidazole / dimethylformamide / 6 h / Ambient temperature 4: 1.) 50 percent NaH, ethyl oxalate; 2.) K2CO3 / 1.) oil, THF, EtOH, 4 h, r.t.; 2.) oil, THF, H2O, 1.5 h, 0 deg C 5: 79.8 percent / acetic acid; tetrahydrofuran; H2O / 72 h / Ambient temperature View Scheme

in tetrahydrofuran; water; acetic acid 72 h; Ambient temperature;

1: imidazole / dimethylformamide / 6 h / Ambient temperature 2: 1.) 50 percent NaH, ethyl oxalate; 2.) K2CO3 / 1.) oil, THF, EtOH, 4 h, r.t.; 2.) oil, THF, H2O, 1.5 h, 0 deg C 3: 79.8 percent / acetic acid; tetrahydrofuran; H2O / 72 h / Ambient temperature View Scheme

1: 94 percent / p-TsOH / benzene / 1 h / Heating 2: imidazole / dimethylformamide / 6 h / Ambient temperature 3: 1.) 50 percent NaH, ethyl oxalate; 2.) K2CO3 / 1.) oil, THF, EtOH, 4 h, r.t.; 2.) oil, THF, H2O, 1.5 h, 0 deg C 4: 79.8 percent / acetic acid; tetrahydrofuran; H2O / 72 h / Ambient temperature View Scheme

1: 1.) 50 percent NaH, ethyl oxalate; 2.) K2CO3 / 1.) oil, THF, EtOH, 4 h, r.t.; 2.) oil, THF, H2O, 1.5 h, 0 deg C 2: 79.8 percent / acetic acid; tetrahydrofuran; H2O / 72 h / Ambient temperature View Scheme