Multi-step reaction with 10 steps
1.1: NaHMDS / diethyl ether; tetrahydrofuran / 0.83 h / -78 °C
1.2: 77 percent / diethyl ether; tetrahydrofuran / 4 h / -78 °C
2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C
2.2: 78 percent / tetrahydrofuran / 2.83 h / -78 - -15 °C
3.1: CF3COOH / methanol / 2 h / 20 °C
4.1: 0.130 g / triethylamine; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 0 °C
5.1: 100 percent / H2 / Pd/C / methanol / 2 h
6.1: 94 percent / p-carboxybenzenesulfonyl azide; triethylamine / acetonitrile / 2 h
7.1: Rh2(OAc)4 / CH2Cl2 / 2 h / 20 °C
8.1: 61 percent / LiAlH4 / tetrahydrofuran / 78 h / -78 - 70 °C
9.1: I2; Ph3P; imidazole / CH2Cl2 / 4 h / 0 °C
10.1: CuI / tetrahydrofuran; cyclohexane; diethyl ether / 0.17 h / 0 °C
10.2: 0.016 g / tetrahydrofuran; cyclohexane; diethyl ether / 8 h / 20 °C
With
1H-imidazole; dmap; dirhodium tetraacetate; copper(l) iodide; lithium aluminium tetrahydride; p-carboxybenzenesulfonyl azide; hydrogen; iodine; sodium hexamethyldisilazane; triethylamine; triphenylphosphine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; acetonitrile;
DOI:10.1016/j.tet.2004.03.094