Multi-step reaction with 14 steps
1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C
1.2: 99 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.1: 97 percent / LiBH4 / tetrahydrofuran / 1 h / 20 °C
3.1: 70 percent / 4-dimethylaminopyridine; triethylamine / CH2Cl2 / 5 h / 20 °C
4.1: 78 percent / triphenylphosphine; carbon tetrabromide / CH2Cl2 / 1 h / 20 °C
5.1: 72 percent / acetonitrile / 12 h / 20 °C
6.1: 89 percent / triethylamine / tetrahydrofuran / 3 h / 50 °C
7.1: 96 percent / (1,3-dimesitylimidazolidin-2-yl)[P(c-hexyl)3]Ru(=CHPh)Cl2 / CH2Cl2 / 3 h / 45 °C
8.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
9.1: BH3 / tetrahydrofuran / 15 h / 20 °C
9.2: NaBO3*4H2O / tetrahydrofuran; H2O / 2 h / 20 °C
9.3: 1.87 g / manganese dioxide / CH2Cl2 / 2 h / 20 °C
10.1: triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C
10.2: HCl / ethyl acetate / 20 °C
11.1: 1.20 g / triethylamine / tetrahydrofuran / 1 h / 20 °C
12.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
12.2: 98 percent / tetrahydrofuran / 1 h / -78 °C
13.1: 65 percent / Pd2(dba)3*CHCl3; LiCl; Ph3As / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C
14.1: HCl / ethyl acetate / 12 h / 20 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; lithium borohydride; carbon tetrabromide; triphenyl-arsane; borane; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile;
10.1: Mitsunobu reaction / 13.1: Stille reaction;
DOI:10.1016/S0968-0896(03)00452-8