Multi-step reaction with 11 steps
2.1: tetramethylethylenediamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 76 percent / I2 / tetrahydrofuran; hexane / 1 h / -78 °C
3.1: 63 percent / NaOH; water / methanol / Heating
4.1: 59 percent / 0.5 h / 70 °C
5.1: 90 percent / CuI; triethylamine / PdCl2(PPh3)2 / tetrahydrofuran / 1 h / 20 °C
6.1: 54 percent / tetrabutylammonium fluoride; H2O / tetrahydrofuran / 1 h / 20 °C
7.1: CuI; triethylamine / PdCl2(PPh3)2 / tetrahydrofuran / 1 h / 20 °C
8.1: 42 percent / H2 / Pd/C; quinoline / ethyl acetate / 2 h / 20 °C / 760.05 Torr
9.1: 87 percent / NaHCO3; H2O / methanol / 1.5 h / 20 °C
10.1: 70 percent / triethylamine / CH2Cl2 / 20 °C
11.1: (R)-(+)-BINAP; triethylamine / Pd(OAc)2 / acetonitrile / 181 h / 60 °C
11.2: H2 / Pd/C / ethanol / 48 h / 760.05 Torr
With
sodium hydroxide; copper(l) iodide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydrogencarbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triethylamine;
quinoline; bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;
1.1: Addition / 2.1: Metallation / 2.2: Iodination / 3.1: Hydrolysis / 4.1: Acetylation / 5.1: catalyzed coupling / 6.1: Hydrolysis / 7.1: catalyzed coupling / 8.1: Catalytic hydrogenation / 9.1: Hydrolysis / 10.1: Addition / 11.1: Cyclization / 11.2: Catalytic hydrogenation;
DOI:10.1021/ol006056f