1: LDA / tetrahydrofuran / 1.) -33 deg C, 5 min, 2.) -120 deg C 2: pyridine / CH2Cl2 / 0 - 25 °C 3: HCl / methanol / 0 °C 4: 1.) 9-BBN, 2.) Ph3As, Cs2CO3, H2O / 2.) <Pd(dppf)Cl2> / 1.) THF, 2.) DMF 5: HCl / methanol 6: 88 percent / H2, HCl / <(R)-(binap)RuCl2> / methanol / 7 h / 25 °C / 62255 Torr 7: 2,6-lutidine / CH2Cl2 / -78 - 25 °C 8: HCl / methanol 9: 78 percent / 2,4,6-trichlorobenzoyl chloride, Et3N, 4-DMAP / toluene 10: 95 percent / SmI2 / NiI2 / tetrahydrofuran / -78 °C 11: 98 percent / HF*pyridine / tetrahydrofuran 12: 98 percent / 3,3-dimethyldioxirane / CH2Cl2 / -50 °C View Scheme

1: LDA / tetrahydrofuran / 1.) -33 deg C, 5 min, 2.) -120 deg C 2: pyridine / CH2Cl2 / 0 - 25 °C 3: HCl / methanol / 0 °C 4: 1.) 9-BBN, 2.) Ph3As, Cs2CO3, H2O / 2.) <Pd(dppf)Cl2> / 1.) THF, 2.) DMF 5: HCl / methanol 6: 88 percent / H2, HCl / <(R)-(binap)RuCl2> / methanol / 7 h / 25 °C / 62255 Torr 7: 2,6-lutidine / CH2Cl2 / -78 - 25 °C 8: HCl / methanol 9: 78 percent / 2,4,6-trichlorobenzoyl chloride, Et3N, 4-DMAP / toluene 10: 95 percent / SmI2 / NiI2 / tetrahydrofuran / -78 °C 11: 98 percent / HF*pyridine / tetrahydrofuran View Scheme