Multi-step reaction with 8 steps
1: 94 percent / pyridinium chlorochromate, Florisil / CH2Cl2 / 1 h / Ambient temperature
2: 1.) 1.6 M t-butyl-lithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, 30 min
3: 60 percent / 1,2-dichloro-benzene / 40 h / Heating
4: 1.) ozone; 2.) NaBH4 / 1.) methanol, CH2Cl2, -78 deg C, 3 min; 2.) methanol, CH2Cl2, 45 min, RT
5: 93 percent / pyridine, lead tetra-acetate / benzene / 2 h / Ambient temperature
6: 1.) 1.56 M n-butyl-lithium / 1.) THF, hexane, -78 deg C, 1 h; 2.) THF, hexane, -78 deg C, 2.5 h
7: tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature
8: 56 percent / 1.) triethylamine / CH2Cl2 / 1.) , -78 deg C, 30 min, 2.) -40 deg C, 30 min
With
pyridine; lead(IV) acetate; sodium tetrahydroborate; florisil; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; ozone; triethylamine; pyridinium chlorochromate;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-benzene; benzene;