triphenylphosphine; palladium diacetate in toluene T=100°C; 1 h;

hydrogenchloride in methanol 48 h; Ambient temperature;

dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 15 min, 3.) -78 deg C, 11 min;

1: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 2: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: 1) trimethyl orthoformate, Montmorillonite K 10, 2) TsOH / 1) methanol, 20 deg C, 24 h, 2) benzene, reflux, 2 h 2: 84 percent / RuCl3*3H2O, NaIO4 / acetonitrile; CCl4; H2O / 24 h / 20 °C 3: MeONa / methanol / 15 h / Heating 4: 95 percent / triethylamine, 4-dimethylaminopyridine / dimethylformamide / 6 h / 20 °C 5: 1N NaOH / tetrahydrofuran; methanol / 2 h / 20 °C 6: 1) LDA / 1) THF, -78 deg C, 1 h, 2) -78 deg C to 0 deg C, 2 h 7: DCC, DMAP, Et3N / CH2Cl2 / 2 h / 20 °C 8: nBu4NF / tetrahydrofuran / 2 h / 20 °C 9: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 10: MeONa / methanol / 1 h / 20 °C 11: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 12: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 2: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: 95 percent / triethylamine, 4-dimethylaminopyridine / dimethylformamide / 6 h / 20 °C 2: 1N NaOH / tetrahydrofuran; methanol / 2 h / 20 °C 3: 1) LDA / 1) THF, -78 deg C, 1 h, 2) -78 deg C to 0 deg C, 2 h 4: DCC, DMAP, Et3N / CH2Cl2 / 2 h / 20 °C 5: nBu4NF / tetrahydrofuran / 2 h / 20 °C 6: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 7: MeONa / methanol / 1 h / 20 °C 8: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 9: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 2: MeONa / methanol / 1 h / 20 °C 3: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 4: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: MeONa / methanol / 1 h / 20 °C 2: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 3: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: DCC, DMAP, Et3N / CH2Cl2 / 2 h / 20 °C 2: nBu4NF / tetrahydrofuran / 2 h / 20 °C 3: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 4: MeONa / methanol / 1 h / 20 °C 5: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 6: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme