Multi-step reaction with 9 steps
1: NH4OAc, Cu(OAc)2 / acetic acid / 24 h / Heating
2: LiAlH4 / tetrahydrofuran / 6 h / Ambient temperature
3: Dess-Martin periodinane, tert-butyl alcohol / CH2Cl2 / 0.5 h / Ambient temperature
4: triphenylphosphine / CH2Cl2 / 0.42 h / Ambient temperature
5: n-BuLi / tetrahydrofuran / 1 h / -78 °C
6: 1.) AIBN, tri-n-butyltin hydride, 2.) I2 / 1.) 120 deg C - 140 deg C, 3 h, 2.) Et2O, RT, 45 min
7: 1.) tert-butyllithium / 1.) THF, pentane, -100 deg C, 25 min, 2.) THF, pentane, from -100 deg C to -78 deg C, 30 min
8: tetra-n-butylammonium fluoride, HOAc / tetrahydrofuran / 19 h / Ambient temperature
9: H2 / 10percent Pd/C / methanol / 72 h / 2585.7 Torr
With
lithium aluminium tetrahydride; n-butyllithium; copper diacetate; 2,2'-azobis(isobutyronitrile); ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; Dess-Martin periodane; acetic acid; triphenylphosphine; tert-butyl alcohol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid;
DOI:10.1021/jm00113a019