Multi-step reaction with 8 steps
1: 1.) NaH / 1.) DME, RT, 30 min, 2.) reflux, 18 h
2: 93 percent / n-Bu4NF / tetrahydrofuran / 16 h / Ambient temperature
3: 94 percent / MnO2 / CH2Cl2 / 24 h / Ambient temperature
4: 1.) n-BuLi / 1.) THF, hexane, a) -78 deg C, 2 h, b) -10 deg C, 1 h, 2.) -78 deg C to RT, 4 h
5: 100 percent / n-Bu4NF / tetrahydrofuran / 20 h / Ambient temperature
6: 100 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 4 h / Ambient temperature
7: 1.) t-BuOOH, VO(acac)2, 2.) n-Bu4NF / 1.) benzene, 60 deg C, 3 h, 2.) THF, RT, 16 h
8: 1.) zinc tosylate, Ph3P, diethyl azodicarboxylate (DEAD), 2.) t-BuOK / 1.) benzene, RT, 3 h, 2.) DMF, 35 deg C, 1.5 h
With
tert.-butylhydroperoxide; dmap; manganese(IV) oxide; n-butyllithium; bis(acetylacetonate)oxovanadium; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; zinc(II) tosylate; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00008a044