Multi-step reaction with 12 steps
1: Et3N / diethyl ether / 2 h / 0 °C
2: 1.) n-BuLi / 1.) THF, hexane, 2.) THF, from -78 deg to RT, 1 h
3: 1.) LDA / 1) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -10 deg C, 2 h
4: 83 percent / LiBH4, H2O / diethyl ether; tetrahydrofuran / 0.5 h / 0 - 20 °C
5: 100 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, reflux, 18 h
7: aq. KOH / dioxane / 18 h / Ambient temperature
8: 3 h / 125 - 140 °C
9: diethyl ether / 0.17 h / 0 °C
10: 1.) 9-BBN, 2.) tetrakis(triphenylphosphine)palladium(0), K3PO4 / 1.) THF, RT, 18 h, 2.) THF, reflux, 47 h
11: 92 percent / 20percent palladium hydroxide/C / cyclohexane / 25 h / Heating
12: 100 percent / Ph3P, diethyl azodicarboxylate (DEAD) / CH2Cl2 / 1.17 h
With
potassium hydroxide; potassium phosphate; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; palladium hydroxide - carbon; water; sodium hydride; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; cyclohexane;
DOI:10.1021/jm00054a003