Multi-step reaction with 18 steps
1: 76 percent / propionic acid / xylene / 3 h / Heating
2: 100 percent / H2 / PtO2 / hexane / 30 h / 760 Torr
3: 6.7 g / LAH / diethyl ether / 0.5 h / Ambient temperature
4: 98 percent / imidazole / dimethylformamide / 1 h
5: 89 percent / 0.67 h / Heating
6: 50 percent / N-bromosuccinimide (NBS), aq. HClO4 / 1.5 h / 0 - 20 °C
7: 75 percent / Pb(OAc)4, CaCO3, I2 / cyclohexane / 3 h / Heating; Irradiation
8: 1.10 g / KOH / methanol / 0.5 h / Heating
9: 8 N Jones' reagent / acetone / 1 h / 0 °C
10: 62 percent / Zn, i-PrOH / dimethylformamide / 8 h / Heating
11: 89 percent / 8 N Jones' reagent / acetone / 2 h / 0 °C
12: 86 percent / triethylamine (TEA) / 0.5 h / Heating
13: 83 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH2Cl2 / 5 h / -78 - -23 °C
14: 76 percent / TBAF / tetrahydrofuran / 18 h
15: pyridine, DMAP / 22 h
16: NaBH4 / dimethylsulfoxide / 3 h / 85 °C
17: PhI(OOCCF3)2, H2O / ethanol / 0.17 h / Ambient temperature
18: TsOH / methanol / 0.25 h / Heating
With
pyridine; 1H-imidazole; lead(IV) acetate; dmap; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; perchloric acid; jones' reagent; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; toluene-4-sulfonic acid; propionic acid; triethylamine; isopropyl alcohol; bis-[(trifluoroacetoxy)iodo]benzene; calcium carbonate; zinc;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; cyclohexane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; xylene;