Multi-step reaction with 9 steps
1: 75 percent / Et3N / CH2Cl2 / 0.33 h / -15 °C
2: 90 percent / 2M NaOMe / CH2Cl2; methanol / 20 h / 20 °C
3: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating
4: 1) 1.4 M Na-methylsulfinylmethanide / 1) methyl sulfoxide, 0.5 h, 2) 1 h
5: 80 percent / PdCl2, Na-acetate / acetic acid; H2O / Ambient temperature
6: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -65 deg C, 15 min.
7: 1) BuLi / 1) oxolane, hexane, 2.5 h, 2) oxolane, -70 deg C, 3 h
8: 91 percent / HgCl2, CdCO3 / acetone; H2O / 8 h / Heating
9: 27.3 percent / NaBH4 / methanol / 0.5 h
With
sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; dimsylsodium; sodium methylate; sodium acetate; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium dichloride;
In
methanol; diethyl ether; dichloromethane; water; acetic acid; acetone;
DOI:10.1016/S0008-6215(00)90496-8