1: potassium tert-butylate; (methoxymethyl)-triphenylphosphonium chloride in tetrahydrofuran T=20°C; 0.0833333 h; 2: C20H22N2O4 in tetrahydrofuran T=-78 - 20°C; Wittig Olefination; 3: With trifluoroacetic acid; trifluoroacetic anhydride in dichloromethane T=20°C; 20 h;

1.1: triethylamine / acetonitrile / 2.33 h / 20 °C 2.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / |Inert atmosphere 3.1: 6 h / 0 °C 4.1: tetrahydrofuran / 0.08 h / 20 °C 4.2: -78 - 20 °C View Scheme

1.1: ozone / dichloromethane / -78 °C 1.2: -78 °C 2.1: triethylamine / acetonitrile / 2.33 h / 20 °C 3.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / |Inert atmosphere 4.1: 6 h / 0 °C 5.1: tetrahydrofuran / 0.08 h / 20 °C 5.2: -78 - 20 °C View Scheme

1.1: triethylamine 2.1: potassium carbonate / dimethyl sulfoxide / 4 h / 20 °C 3.1: water; N-chloro-succinimide / tetrahydrofuran / -18 - 20 °C 4.1: thiophenol; potassium carbonate / dimethyl sulfoxide / 2.15 h 5.1: triethylamine / acetonitrile / 2.33 h / 20 °C 6.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / |Inert atmosphere 7.1: 6 h / 0 °C 8.1: tetrahydrofuran / 0.08 h / 20 °C 8.2: -78 - 20 °C View Scheme

1.1: triethylamine / acetonitrile / 2.33 h / 20 °C 2.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / |Inert atmosphere 3.1: 6 h / 0 °C 4.1: tetrahydrofuran / 0.08 h / 20 °C 4.2: -78 - 20 °C View Scheme

1: potassium tert-butylate; (methoxymethyl)-triphenylphosphonium chloride in tetrahydrofuran T=20°C; 0.0833333 h; 2: C20H22N2O4 in tetrahydrofuran T=-78 - 20°C; Wittig Olefination;

palladium 10 on activated carbon; hydrogen in ethyl acetate P=760.051 Torr; 18 h;

palladium 10 on activated carbon; hydrogen in ethyl acetate P=760.051 Torr; 18 h;

With  palladium 10 on activated carbon; hydrogen in  ethyl acetate P=760.051 Torr; 18 h;