Multi-step reaction with 9 steps
1: 75 percent / K2CO3 / dimethylformamide / 20 h / Ambient temperature
2: 95 percent / NaOH / H2O / 12 h / 100 °C
3: 99 percent / CDI, DBU / dimethylformamide / 60 h / 40 °C
4: 48 percent / BuLi / tetrahydrofuran; hexane / 1.) -70 deg C, 10 min, 2.) -78 deg C, 20 min; warm to room temperature, 45 min
5: DMF, (COCl)2 / CH2Cl2 / 3 h / Ambient temperature
6: 81 percent / t-BuOK / tetrahydrofuran / 0.75 h / 0 °C
7: 51 percent / BuLi / tetrahydrofuran; hexane / 1 h / -72 °C
8: 97 percent / PDC / dimethylformamide / 8 h / Ambient temperature
9: 100 percent / Bu4NMnO4 / pyridine / 44 h / Ambient temperature
With
sodium hydroxide; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; tetra-n-butylammonium permanganate; potassium tert-butylate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; 1,1'-carbonyldiimidazole;
In
tetrahydrofuran; pyridine; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo952280k