Multi-step reaction with 11 steps
1: NaH
2: nBu4NF / tetrahydrofuran
3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2) CH2Cl2, -78 to 0 deg C
4: 1) CuBr*Me2S / 1) Et2O, -78 deg C, 2) Et2O, -78 to 20 deg C
5: AcOH, H2O / tetrahydrofuran
6: pyridine / 0 °C
7: K2CO3 / methanol
8: AcOH / CH2Cl2 / Ambient temperature
9: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2) CH2Cl2, -78 to 0 deg C
10: CH2Cl2; diethyl ether
11: 1) (COCl)2, DMSO, 2) Et3N / 1) -78 deg C, 2) -78 to 0 deg C
With
pyridine; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)77159-0