Multi-step reaction with 12 steps
1.1: copper(I) iodide / tetrahydrofuran; diethyl ether / 0 °C
1.2: tetrahydrofuran; diethyl ether / 1 h / -78 - -45 °C
1.3: 95 percent / iodine / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 °C
2.1: DIBAL-H / CH2Cl2; hexane / 2 h / -78 °C
3.1: 100 percent / imidazole / CH2Cl2 / 15 h / 20 °C
4.1: 75 percent / Et3N / bis(triphenylphosphine)palladium(II) dichloride / 1-methyl-pyrrolidin-2-one / 44 h / 70 °C / 15514.4 Torr
5.1: 66 percent / DIBAL-H / toluene / 1.5 h / -78 °C
6.1: 100 percent / imidazole / CH2Cl2 / 0 - 20 °C
7.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1.08 h / 20 °C
8.1: triethylamine / CH2Cl2 / 1.5 h / 0 °C
9.1: 5.09 g / sodium iodide / acetone / 2.5 h / Heating
10.1: t-butyllithium / tetrahydrofuran; pentane / 2 h / -78 °C
10.2: 62 percent / tetrahydrofuran; pentane / 16 h / -100 - -78 °C
11.1: 90 percent / aqueous oxalic acid / diethyl ether / 2.5 h / 20 °C
12.1: diethyl cyanophosphonate / tetrahydrofuran / 1 h / 20 °C
12.2: samarium; diiodoethane; methanol / tetrahydrofuran / 2 h / 23 °C
With
1H-imidazole; copper(l) iodide; diethyl cyanophosphonate; tert.-butyl lithium; oxalic acid; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; hexane; dichloromethane; water; acetone; toluene; pentane;
DOI:10.1016/S0040-4020(03)00372-7