Multi-step reaction with 11 steps
2: 79.1 percent / NaOAc, pyridinium chlorochromate (PCC) / CH2Cl2 / 0.83 h / Ambient temperature
3: 97.7 percent / n-BuLi / tetrahydrofuran; hexane / 0.67 h
4: 83.5 percent / NaOAc, pyridinium chlorochromate (PCC) / CH2Cl2 / 4 h / Ambient temperature
5: 75.2 percent / trimethylortoformate, / p-toluenesulfonic acid / benzene / 1., room temperature, overnight 2.) reflux, 5 h
6: 85.3 percent / n-Bu4NF.3H2O / tetrahydrofuran / 6 h / Ambient temperature
7: 84.9 percent / NaOAc, pyridinium chlorochromate (PCC) / CH2Cl2 / 0.75 h / Ambient temperature
8: 60.6 percent / samarium(II) iodide / tetrahydrofuran; various solvent(s) / -78 - -10 °C
9: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, 1 h, 0 deg C 2.) THF, hexane, dimethyltetrahydropyrimidinone
10: 72.4 percent / DDQ, 2,6-lutidine / benzene / 20 h / Heating
11: 52.4 percent / water, K2CO3, 30percent H2O2 / CH2Cl2 / 42 h / Ambient temperature
With
2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium acetate; potassium carbonate; diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trimethyl orthoformate;
samarium diiodide; toluene-4-sulfonic acid;
In
tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1021/ja00223a026