Multi-step reaction with 7 steps
1: 1.) 1.6M BuLi / 1.) THF, hexane, 0 deg C, 10 min; 2.) 0 deg C, 30 min
2: AcONa, molecular sieve (3 Angstroem), Al2O3, pyridinium chlorochromate / CH2Cl2 / 6 h
3: trimethylorthoformate, p-toluenesulfonic acid monohydrate / benzene / 1.) 6 h, RT; 2.) 6 h, reflux
4: Bu4NF*3H2O / tetrahydrofuran / 12 h / Ambient temperature
5: 79 percent / AcONa, molecular sieve (3 Angstroem), Al2O3, pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature
6: SmI2, HMPT, tBuOH / tetrahydrofuran / 0.17 h / 0 °C
7: p-toluenesulfonic acid monohydrate / acetone / 12 h / Ambient temperature
With
N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum oxide; n-butyllithium; samarium diiodide; 3 A molecular sieve; tetrabutyl ammonium fluoride; sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate; tert-butyl alcohol; trimethyl orthoformate;
In
tetrahydrofuran; dichloromethane; acetone; benzene;