Multi-step reaction with 11 steps
1: 86 percent / BuLi / tetrahydrofuran / 18 h / Heating
2: 1.) dicyclohexylborane, 2.) AcOH / 1.) THF, r.t., 2 h, 2.) THF, r.t., 1 h
3: Br2 / CH2Cl2 / 0.17 h / -78 °C
4: NaOMe / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 2 h
6: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature
7: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
8: LiAlH4 / diethyl ether / 3 h / 0 °C
9: imidazole / dimethylformamide / 1 h / Ambient temperature
10: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
11: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
With
1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; trifluorormethanesulfonic acid; bis(cyclohexanyl)borane; dihydrogen peroxide; bromine; sodium methylate; acetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1039/a804275f