Multi-step reaction with 9 steps
1: 1.) NaCH2SOCH3 / 1.) DMSO, RT, 30 min, 2.) DMSO, RT, 1 h
2: diethyl ether; methanol
3: DIBAL-H / CH2Cl2 / 0.5 h / 0 °C
4: NBS, Ph3P / CH2Cl2 / 0.42 h / 0 - 20 °C
5: dimethylformamide / 2 h / 4A molecular sieves
6: 1.) NaOMe / 1.) MeOH, 10 min, 2.) MeOH, RT, 18 h
7: aq. KH2PO4 / diethyl ether / 18 h / 0 °C
8: aq. HCl / 3.5 h / Heating
9: 87 percent / diethyl ether; methanol / Ambient temperature
With
hydrogenchloride; potassium dihydrogenphosphate; N-Bromosuccinimide; sodium methylate; diisobutylaluminium hydride; sodium methylsulfinylmethanide; triphenylphosphine;
In
methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm960167w