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