Multi-step reaction with 11 steps
1.1: 75 percent / 4-dimethylaminopyridine / 5 h / Heating
2.1: 42 percent / potassium permanganate / H2O / 2.5 h / 50 - 90 °C
3.1: carbonyldiimidazole / dimethylformamide / 0.75 h / 20 °C
3.2: 65 percent / potassium tert-butoxide / dimethylformamide / 2 h / 120 °C
4.1: 55 percent / HBr / H2O / 30 h / Heating
5.1: 94 percent / 4-dimethylaminopyridine / 5 h / Heating
6.1: 54 percent / NaOMe; isoamyl nitrite / methanol / 2 h / 20 °C
7.1: ethanol / 7 h / Heating
8.1: 2.2 g / 2,2,4,4-tetramethylcyclobutane-1,3-dithione / CH2Cl2 / 1 h / 20 °C
9.1: 52 percent / K2CO3 / methanol / 20 h / 20 °C
10.1: 82 percent / HCl / H2O / 14 h / Heating
11.1: NaH / dimethylformamide / 1 h / 20 °C
11.2: 32 percent / dimethylformamide / 8 h / Heating
With
hydrogenchloride; dmap; potassium permanganate; 2,2,4,4-tetramethylcyclobutane-1,3-dithione; hydrogen bromide; sodium methylate; sodium hydride; potassium carbonate; 1,1'-carbonyldiimidazole; isopentyl nitrite;
In
methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo026619w