1: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 2: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 3: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 4: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 5: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

1: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature 2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h 3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 4: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 5: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 6: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 7: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 8: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 9: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 10: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

1: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h 2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 3: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 4: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 5: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 6: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 7: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 8: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 9: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

1: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min 2: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature 3: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h 4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h 5: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min 6: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 7: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 8: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 9: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 10: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 11: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

1: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min 2: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h 3: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 4: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 5: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 6: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

1: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature 2: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature 3: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min 4: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature 5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

1: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT 2: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature 3: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 4: 92 percent / diethyl ether / 0.25 h / Ambient temperature 5: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 6: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 7: aq. HF / acetonitrile / 0.83 h / Ambient temperature 8: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 9: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme

1: 99 percent / aq. HF / acetonitrile / 1.25 h / Ambient temperature 2: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT 3: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature 4: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 5: 92 percent / diethyl ether / 0.25 h / Ambient temperature 6: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 7: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 8: aq. HF / acetonitrile / 0.83 h / Ambient temperature 9: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 10: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme

1: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature 2: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 3: 92 percent / diethyl ether / 0.25 h / Ambient temperature 4: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 5: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 6: aq. HF / acetonitrile / 0.83 h / Ambient temperature 7: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 8: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme

1: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature 2: 92 percent / diethyl ether / 0.25 h / Ambient temperature 3: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature 4: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C 5: aq. HF / acetonitrile / 0.83 h / Ambient temperature 6: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C 7: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature View Scheme