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

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