sodium hydrogencarbonate in diphenylether retro Diels-Alder reaction; 0.5 h; Heating;

1.1: NaBH4; CeCl3 / 0 °C 2.1: pyridine 3.1: BF3*Et2O / toluene 3.2: 90 percent / NaOMe / methanol 4.1: 99 percent / Huenig base / CH2Cl2 5.1: 99 percent / H2 / Pd/C / ethyl acetate 6.1: 89 percent / I2; PPh3; imidazole / tetrahydrofuran 7.1: 98 percent / Zn / acetic acid; methanol / 20 °C 8.1: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C 9.1: H2; quinoline / Pd/BaSO4 / ethyl acetate 10.1: Grubbs' catalyst / benzene / Heating View Scheme

1.1: pyridine 2.1: BF3*Et2O / toluene 2.2: 90 percent / NaOMe / methanol 3.1: 99 percent / Huenig base / CH2Cl2 4.1: 99 percent / H2 / Pd/C / ethyl acetate 5.1: 89 percent / I2; PPh3; imidazole / tetrahydrofuran 6.1: 98 percent / Zn / acetic acid; methanol / 20 °C 7.1: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C 8.1: H2; quinoline / Pd/BaSO4 / ethyl acetate 9.1: Grubbs' catalyst / benzene / Heating View Scheme

1: H2; quinoline / Pd/BaSO4 / ethyl acetate 2: Grubbs' catalyst / benzene / Heating View Scheme

1: 99 percent / Huenig base / CH2Cl2 2: 99 percent / H2 / Pd/C / ethyl acetate 3: 89 percent / I2; PPh3; imidazole / tetrahydrofuran 4: 98 percent / Zn / acetic acid; methanol / 20 °C 5: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C 6: H2; quinoline / Pd/BaSO4 / ethyl acetate 7: Grubbs' catalyst / benzene / Heating View Scheme

1: 89 percent / I2; PPh3; imidazole / tetrahydrofuran 2: 98 percent / Zn / acetic acid; methanol / 20 °C 3: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C 4: H2; quinoline / Pd/BaSO4 / ethyl acetate 5: Grubbs' catalyst / benzene / Heating View Scheme

1: 98 percent / Zn / acetic acid; methanol / 20 °C 2: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C 3: H2; quinoline / Pd/BaSO4 / ethyl acetate 4: Grubbs' catalyst / benzene / Heating View Scheme

1.1: BF3*Et2O / toluene 1.2: 90 percent / NaOMe / methanol 2.1: 99 percent / Huenig base / CH2Cl2 3.1: 99 percent / H2 / Pd/C / ethyl acetate 4.1: 89 percent / I2; PPh3; imidazole / tetrahydrofuran 5.1: 98 percent / Zn / acetic acid; methanol / 20 °C 6.1: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C 7.1: H2; quinoline / Pd/BaSO4 / ethyl acetate 8.1: Grubbs' catalyst / benzene / Heating View Scheme

1: 99 percent / H2 / Pd/C / ethyl acetate 2: 89 percent / I2; PPh3; imidazole / tetrahydrofuran 3: 98 percent / Zn / acetic acid; methanol / 20 °C 4: 60 percent / LDA / tetrahydrofuran / -78 - 20 °C 5: H2; quinoline / Pd/BaSO4 / ethyl acetate 6: Grubbs' catalyst / benzene / Heating View Scheme

1: 95 percent / (i-Pr)2NEt / CH2Cl2 2: 91 percent / Zn; AcOH / methanol 3: 93 percent / NaHCO3 / diphenyl ether / 0.5 h / Heating View Scheme