Multi-step reaction with 13 steps
1: 75 percent / Zn-powder / dimethylformamide / 12 h / 35 °C
2: 38 percent / BF3*Et2O / acetonitrile / 12 h / Ambient temperature
3: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature
4: 94 percent / imidazole / dimethylformamide / 12 h / Ambient temperature
5: 59.7 percent / m-chloroperbenzoic acid, Na2CO3, MgSO4 / CH2Cl2 / 48 h / Ambient temperature
6: 98 percent / Ti(OiPr)4 / 6 h / 32 °C
7: 1) DMSO, (CF3CO)2O 2) Et3N / 1) CH2Cl2, -70 deg C
9: 98 percent / conc. HCl / acetonitrile / 0.75 h / 5 °C
10: 95 percent / Et3N / CH2Cl2 / 0.5 h / 5 °C
11: 98 percent / NaOMe / methanol / 0.33 h / -20 °C
12: 74 percent / toluene / 0.5 h / 105 °C
13: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature
With
1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; boron trifluoride diethyl etherate; sodium methylate; sodium carbonate; magnesium sulfate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; zinc; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1248/cpb.39.663