triethylamine in tetrahydrofuran T=20°C; 18 h;

triethylamine in tetrahydrofuran T=20°C; 18 h;

1.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 2.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 3.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 4.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 5.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 5.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 6.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 6.2: 39 mg / H2 / Pd/C / ethanol / 48 h 7.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 2.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 3.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 4.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 4.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 5.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 5.2: 39 mg / H2 / Pd/C / ethanol / 48 h 6.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 2.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 2.2: 39 mg / H2 / Pd/C / ethanol / 48 h 3.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 2.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 3.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 3.2: 39 mg / H2 / Pd/C / ethanol / 48 h 4.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 2.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 3.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 4.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 4.2: 39 mg / H2 / Pd/C / ethanol / 48 h 5.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 2.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 3.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 4.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 5.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 6.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 6.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 7.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 7.2: 39 mg / H2 / Pd/C / ethanol / 48 h 8.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme

1: 94 percent / H2 / Pd/C / ethanol / 18 h 2: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme