1.1: 74 percent / Et2AlI / hexane; CH2Cl2 / 0.5 h / 0 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 2.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 - 20 °C 3.1: Li / tetrahydrofuran / 26 h 3.2: CuI / tetrahydrofuran / 0.33 h / -20 °C 3.3: 169 mg / tetrahydrofuran / 1 h / -20 °C 4.1: Li / tetrahydrofuran 4.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C 4.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 5.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 6.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 7.1: 54 percent / pyridine / CH2Cl2 / 4 h 8.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 9.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 10.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 11.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 12.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 13.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1.1: Li / tetrahydrofuran 1.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C 1.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 2.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 3.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 4.1: 54 percent / pyridine / CH2Cl2 / 4 h 5.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 6.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 7.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 8.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 9.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 10.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1.1: Li / tetrahydrofuran 1.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C 1.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 2.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 3.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 4.1: 54 percent / pyridine / CH2Cl2 / 4 h 5.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 6.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 7.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 8.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 9.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 10.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 1.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Li / tetrahydrofuran / 26 h 2.2: CuI / tetrahydrofuran / 0.33 h / -20 °C 2.3: 169 mg / tetrahydrofuran / 1 h / -20 °C 3.1: Li / tetrahydrofuran 3.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C 3.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 4.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 5.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 6.1: 54 percent / pyridine / CH2Cl2 / 4 h 7.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 8.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 9.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 10.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 11.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 12.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1.1: Li / tetrahydrofuran / 26 h 1.2: CuI / tetrahydrofuran / 0.33 h / -20 °C 1.3: 169 mg / tetrahydrofuran / 1 h / -20 °C 2.1: Li / tetrahydrofuran 2.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C 2.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 3.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 4.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 5.1: 54 percent / pyridine / CH2Cl2 / 4 h 6.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 7.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 8.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 9.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 10.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 11.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 2: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 3: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 2: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 3: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 4: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 5: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1.1: 92 percent / N,N-4-dimethylaminopyridine; pyridine / CH2Cl2 / 12 h / 0 °C 2.1: 98 percent / DBU / dimethylformamide / 5 h / 100 °C 3.1: Li / tetrahydrofuran 3.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C 3.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 4.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 5.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 6.1: 54 percent / pyridine / CH2Cl2 / 4 h 7.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 8.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 9.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 10.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 11.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 12.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1.1: 98 percent / DBU / dimethylformamide / 5 h / 100 °C 2.1: Li / tetrahydrofuran 2.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C 2.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 3.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 4.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 5.1: 54 percent / pyridine / CH2Cl2 / 4 h 6.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 7.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 8.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 9.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 10.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 11.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 2: 54 percent / pyridine / CH2Cl2 / 4 h 3: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 4: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 5: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 6: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 7: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 8: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme