1: H2 / 5 percent Pd/Al / dioxane 2: 75 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide 3: dimethylformamide / 145 °C 5: 80 percent / diisobutylaluminum hydride / diethyl ether 6: 82 percent / tetrahydrofuran 7: 1) H2; 2) aq. HF / 1) Pd-C View Scheme

1: sulfuric acid / 2 h / Heating 2: N,N-dimethylaniline; AlCl3 / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

1: sulfuric acid / 2 h / Heating 2: N,N-dimethylaniline; AlCl3 / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

1: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 2: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 3: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 4: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 5: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 95 percent / DMAP; EDCI / CH2Cl2 / 24 h / 20 °C 2: 92 percent / Pd(OAc)2; Et3N; Et3SiH / CH2Cl2 / 20 °C View Scheme

1: 95 percent / DMAP; EDCI / CH2Cl2 / 24 h / 20 °C 2: 92 percent / Pd(OAc)2; Et3N; Et3SiH / CH2Cl2 / 20 °C View Scheme

1: 95 percent / DMAP; EDCI / CH2Cl2 / 24 h / 20 °C 2: 92 percent / Pd(OAc)2; Et3N; Et3SiH / CH2Cl2 / 20 °C View Scheme

1: 95 percent / p-toluenesulfonic acid monohydrate / 24 h / Heating 2: 91 percent / H2 / Pd/C / ethanol View Scheme

1: sulfuric acid / 2 h / Heating 2: N,N-dimethylaniline; AlCl3 / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

toluene-4-sulfonic acid 24 h; Heating;