1: 87 percent / H2O / hexane; 1,2-dichloro-ethane / -30 °C 2: 2,6-lutidine / CH2Cl2 / 0.75 h 4: 93 percent / (R,R)-diisopropyl tartrate, 4 Angstroem molecular sieves / toluene / 1.) -78 deg C, 3 h, 2.) r.t., 12 h 5: TBAF / tetrahydrofuran / 0.5 h 6: TsOH / 0.25 h 7: 1.) catecholborane, 2.) H2O2, NaOH / 1.) (PPh3)3RhCl / 1.) THF, 45 min 8: 1.) (COCl)2, DMSO, 2.) Et3N 9: NaH / tetrahydrofuran / 4 h 10: H2 / 10percent Pd/C / ethanol; ethyl acetate / 5 h 11: tetrahydrofuran / 3 h 12: HCl, H2O / tetrahydrofuran / 3 h / 50 °C 13: 90 percent / TsOH / benzene / 0.5 h 14: 94 percent / 2,6-lutidine / CH2Cl2 / 4 h / -78 °C 15: 75 percent / DIBAL-H / CH2Cl2 / 1.5 h / -78 - -15 °C 16: 1.) (COCl)2, DMSO, 2.) Et3N 18: 2,6-lutidine / CH2Cl2 / 4 h / -50 °C 19: DDQ, H2O / CH2Cl2 / 3 h / 0 °C 20: Dess-Martin periodinane 21: Mo(CHMe2Ph)<N(2,6-(i-Pr)2C6H3)><OCMe(CF3)2>2 / benzene / 4 h / 55 °C 22: 60 percent / HF*pyridine / tetrahydrofuran / 3 h 23: 86 percent / dimethyldioxirane / CH2Cl2 / 4 h / -50 °C View Scheme

1: 87 percent / H2O / hexane; 1,2-dichloro-ethane / -30 °C 2: 2,6-lutidine / CH2Cl2 / 0.75 h 4: 93 percent / (R,R)-diisopropyl tartrate, 4 Angstroem molecular sieves / toluene / 1.) -78 deg C, 3 h, 2.) r.t., 12 h 5: TBAF / tetrahydrofuran / 0.5 h 6: TsOH / 0.25 h 7: 1.) catecholborane, 2.) H2O2, NaOH / 1.) (PPh3)3RhCl / 1.) THF, 45 min 8: 1.) (COCl)2, DMSO, 2.) Et3N 9: NaH / tetrahydrofuran / 4 h 10: H2 / 10percent Pd/C / ethanol; ethyl acetate / 5 h 11: tetrahydrofuran / 3 h 12: HCl, H2O / tetrahydrofuran / 3 h / 50 °C 13: 90 percent / TsOH / benzene / 0.5 h 14: 94 percent / 2,6-lutidine / CH2Cl2 / 4 h / -78 °C 15: 75 percent / DIBAL-H / CH2Cl2 / 1.5 h / -78 - -15 °C 16: 1.) (COCl)2, DMSO, 2.) Et3N 18: 2,6-lutidine / CH2Cl2 / 4 h / -50 °C 19: DDQ, H2O / CH2Cl2 / 3 h / 0 °C 20: Dess-Martin periodinane 21: Mo(CHMe2Ph)<N(2,6-(i-Pr)2C6H3)><OCMe(CF3)2>2 / benzene / 4 h / 55 °C 22: 60 percent / HF*pyridine / tetrahydrofuran / 3 h View Scheme