Multi-step reaction with 6 steps
1: 1.) EtMgBr / 1.) Et2O, reflux, 1 h, 2.) 0 deg C
2: 98 percent / H2 / Lindlar catalyst / methanol / 2 h / 760 Torr
3: 1.) titanium tetraisopropoxide, L-(+)-diethyl tartrate, t-butyl hydroperoxide, 2.) NaBH4 / 1.) CH2Cl2, -23 deg C, 20 h, 2.) RT, 30 min
4: 1.) NaH / 1.) THF, -23 deg C, 30 min, 2.) -23 deg C -> 0 deg C, 30 min, then 0 deg C, 2 h
5: 92 percent / LDA / tetrahydrofuran / -78 deg C -> 0 deg C, 15 min, then 0 deg C, 30 min
6: 1.) BuLi / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C -> RT, 1 h, then RT, 30 min
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; diethyl (2R,3R)-tartrate; ethylmagnesium bromide; hydrogen; sodium hydride; lithium diisopropyl amide;
Lindlar's catalyst;
In
tetrahydrofuran; methanol;