Multi-step reaction with 8 steps
1: EtONa / ethanol / 15 h / Ambient temperature
2: EtONa / ethanol / 4.5 h / Ambient temperature
3: NH4OAc, Cu(OAc)2 / acetic acid / 24 h / Heating
4: LiAlH4 / tetrahydrofuran / 6 h / Ambient temperature
5: oxalyl chloride, DMSO / CH2Cl2; tetrahydrofuran / 0.25 h / -78 °C
6: triphenylphosphine / CH2Cl2 / 0.42 h / Ambient temperature
7: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
8: 1.) AIBN, tri-n-butyltin hydride, 2.) I2 / 1.) 120 deg C - 140 deg C, 3 h, 2.) Et2O, RT, 45 min
With
lithium aluminium tetrahydride; n-butyllithium; copper diacetate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); ammonium acetate; iodine; tri-n-butyl-tin hydride; sodium ethanolate; dimethyl sulfoxide; triphenylphosphine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid;
DOI:10.1021/jm00113a019