Multi-step reaction with 13 steps
1: 99 percent / diisopropylethylamine / CH2Cl2
2: 85 percent / HOAc/THF/H2O (1:1:1) / 48 h / 50 °C
3: 65 percent / NBu4Br, 4 N NaOH / CH2Cl2 / 72 h
4: 1) NaH / 1) DMF, 2) DMF, room temp., 4 h
5: 8.6 g / THF/H2O/3 N HCl (1:1:1) / 3 h / 60 °C
6: 87 percent / pyridine / 12 h
7: 82 percent / H2SO4 / acetic anhydride / 5 h / Ambient temperature
8: 1) TiBr4, 2) NaOAc / 1) dichloromethane/ethyl acetate, 1 h, 2) dichloromethane/ethyl acetate/toluene/acetonitrile
9: 73 percent / 1) Ag-silicate (molecular sieve 4 Angstroem) / 1) dichloromethane, 1 h, 2) dichloromethane/toluene, room temp., 2 h
10: 97 percent / NaOMe (1 percent) / methanol / 4 h / Ambient temperature
11: 72 percent / 1) Ag-silicate (molecular sieve 4 Angstroem) / 1) dichloromethane, 1 h, 2) dichloromethane/toluene, room temp., 3 h
12: 1) tris(triphenylphosphan)rhodium(I)-chlorid, DBO, 2) Hg2O/HgCl2/acetone (10 percent) / 1) toluene/ethanol/H2O, 80 deg C, 1 d, 2) H2O, room temp., 3 h
13: 93 percent / CF3COOH / aq. acetic acid / 3 h / 50 °C
With
tetrahydrofuran; hydrogenchloride; sodium hydroxide; Wilkinson's catalyst; mercury(I) oxide; 4 A molecular sieve; sulfuric acid; tetrabutylammomium bromide; water; sodium methylate; sodium acetate; titanium(IV) bromide; sodium hydride; 2,3-diazabicyclo<2.2.2>oct-2-ene; acetic acid; N-ethyl-N,N-diisopropylamine; acetone; trifluoroacetic acid; mercury dichloride;
In
pyridine; methanol; dichloromethane; acetic anhydride; acetic acid;