1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h 2: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h 3: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C 4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr 5: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C 6: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C 7: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C 8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 9: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 10: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 11: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 12: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 13: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 14: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 15: tetrahydrofuran; hexane / 1.5 h / 25 °C 16: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 17: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 18: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 19: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h 20: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 21: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 22: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

Multi-step reaction with 21 steps 1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h2: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h3: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr5: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C6: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C7: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min9: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C10: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min11: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C12: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr13: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C14: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h15: tetrahydrofuran; hexane / 1.5 h / 25 °C16: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C17: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C18: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C19: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h20: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h21: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C  

Multi-step reaction with 7 steps 1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h2: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h3: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr5: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C6: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C7: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C  

Multi-step reaction with 12 steps 1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h2: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h3: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr5: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C6: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C7: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min9: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C10: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min11: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C12: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr  

Multi-step reaction with 3 steps 1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h2: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h3: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C  

Multi-step reaction with 11 steps 1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h2: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h3: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr5: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C6: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C7: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min9: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C10: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min11: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C