methanol; sodium methylate T=0°C; 2 h;

1: CsF/2-bromopyridiniumtetrafluoroborate / CH2Cl2 2: Bu4NF / tetrahydrofuran / 0.5 h / 0 °C 3: 50 percent / 1.) 2,4,6-trichlorobenzoyl chloride (TCBACl), NEt3; 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF; 2.) PhCH3, 110 deg C 4: pyridinium p-toluenesulfonate (PPTS) / methanol / 50 °C View Scheme

1: H2 / Lindlar / methanol 2: 87 percent / t-BuOOH, d-diethyl tartrate, Ti(O-i-Pr)4 / CH2Cl2 / -20 °C 3: 79 percent / NaIO4 / RuCl3 / CCl4; acetonitrile; H2O 4: 87 percent / petroleum ether / 40 h / 25 °C 5: 90 percent / pyridine 6: 95 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 7: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 8: Bu4NF / tetrahydrofuran / 3 h / 25 °C 9: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 10: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: 87 percent / t-BuOOH, d-diethyl tartrate, Ti(O-i-Pr)4 / CH2Cl2 / -20 °C 2: 79 percent / NaIO4 / RuCl3 / CCl4; acetonitrile; H2O 3: 87 percent / petroleum ether / 40 h / 25 °C 4: 90 percent / pyridine 5: 95 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 6: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 7: Bu4NF / tetrahydrofuran / 3 h / 25 °C 8: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 9: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: 79 percent / NaIO4 / RuCl3 / CCl4; acetonitrile; H2O 2: 87 percent / petroleum ether / 40 h / 25 °C 3: 90 percent / pyridine 4: 95 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 5: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 6: Bu4NF / tetrahydrofuran / 3 h / 25 °C 7: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 8: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: 87 percent / petroleum ether / 40 h / 25 °C 2: 90 percent / pyridine 3: 95 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 4: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 5: Bu4NF / tetrahydrofuran / 3 h / 25 °C 6: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 7: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: 90 percent / pyridine 2: 95 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 3: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 4: Bu4NF / tetrahydrofuran / 3 h / 25 °C 5: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 6: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: 95 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 2: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 3: Bu4NF / tetrahydrofuran / 3 h / 25 °C 4: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 5: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 2: Bu4NF / tetrahydrofuran / 3 h / 25 °C 3: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 4: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: Bu4NF / tetrahydrofuran / 3 h / 25 °C 2: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 3: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme