1: H2; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr 2: 190 mg / CrCl2 / tetrahydrofuran / 20 °C 3: 96 percent / Pd(OAc)2; Ag2CO3; Et3N / CH2Cl2 / 24 h / 20 °C 4: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C 5: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH2Cl2 / 2 h / -10 °C 6: PPh3; DEAD / tetrahydrofuran / 3 h / 20 °C 7: 93 mg / ammonium molybdate; aq. H2O2 / ethanol; tetrahydrofuran / 20 °C 8: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C 9: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 10: 87 percent / O2; NaHCO3 / Pt / H2O; acetone; propan-2-ol / 50 °C View Scheme