cis,cis,cis-tetrakis[(diphenylphosphanyl)methyl]cyclopentane; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) in xylene T=130°C; Suzuki reaction; 20 h;

bis(η3-allyl-μ-chloropalladium(II)); Tedicyp; potassium carbonate in N,N-dimethyl-formamide T=80°C; Suzuki cross-coupling; 20 h;

tetrabutyl ammonium fluoride in acetonitrile T=20 - 25°C; Further byproducts given;

tetrabutyl ammonium fluoride in acetonitrile T=20 - 25°C; Further byproducts given;

fluoride in acetonitrile T=20 - 25°C; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 1) n-BuLi / 1) Et2O, hexane, 0 deg C to room temperature; reflux, 24 h, 2) Et2O, hexane, -78 deg C to room temperature; room temperature, 2 h 2: 112.6 g / 10percent H2SO4 / diethyl ether; hexane 3: 95 percent / PBr3 / diethyl ether / 2 h / Ambient temperature 4: 80 percent / various solvent(s) / 5.5 h / 80 - 100 °C 5: 1) n-BuLi, 2) HMPA / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C 6: 1) n-BuLi / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C to room temperature 7: TBAF, ethyl acrylate / acetonitrile / 0.83 h View Scheme

1: 95 percent / PBr3 / diethyl ether / 2 h / Ambient temperature 2: 80 percent / various solvent(s) / 5.5 h / 80 - 100 °C 3: 1) n-BuLi, 2) HMPA / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C 4: 1) n-BuLi / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C to room temperature 5: TBAF, ethyl acrylate / acetonitrile / 0.83 h View Scheme

1: 80 percent / various solvent(s) / 5.5 h / 80 - 100 °C 2: 1) n-BuLi, 2) HMPA / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C 3: 1) n-BuLi / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C to room temperature 4: TBAF, ethyl acrylate / acetonitrile / 0.83 h View Scheme

1: 1) n-BuLi, 2) HMPA / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C 2: 1) n-BuLi / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C to room temperature 3: TBAF, ethyl acrylate / acetonitrile / 0.83 h View Scheme

tetrabutyl ammonium fluoride; acrylic acid methyl ester in acetonitrile 0.666667 h; Further byproducts given. Title compound not separated from byproducts;