triethylamine in dichloromethane 0.166667 h;

sodium iodide in acetone T=0°C; 1.5 h; Yield given;

1: NaI / acetone / 1.5 h / 0 °C 2: 1.) NaOMe / 1.) MeOH, r.t., 30 min, 2.) MeOH, r.t., 4 h, reflux, 1.5 h 3: NaBH4 / methanol / 0.33 h / -55 °C 4: 1.) DIBAL, 2.) NaBH4 / 1.) toluene, -78 deg C, 1.5 h, 2.) MeOH, -30 deg C, 20 min 5: CH2Cl2; pyridine / 1 h / Ambient temperature View Scheme

1: NaI / acetone / 1.5 h / 0 °C 2: 1.) NaOMe / 1.) MeOH, r.t., 30 min, 2.) MeOH, r.t., 4 h, reflux, 1.5 h 3: NaBH4 / methanol / 0.33 h / -55 °C 4: 1.) DIBAL, 2.) NaBH4 / 1.) toluene, -78 deg C, 1.5 h, 2.) MeOH, -30 deg C, 20 min 5: CH2Cl2; pyridine / 1 h / Ambient temperature 6: 80 percent / 2.5 h / Ambient temperature; HMPT View Scheme

1: NaI / acetone / 1.5 h / 0 °C 2: 1.) NaOMe / 1.) MeOH, r.t., 30 min, 2.) MeOH, r.t., 4 h, reflux, 1.5 h View Scheme

1: NaI / acetone / 1.5 h / 0 °C 2: 1.) NaOMe / 1.) MeOH, r.t., 30 min, 2.) MeOH, r.t., 4 h, reflux, 1.5 h 3: NaBH4 / methanol / 0.33 h / -55 °C 4: 1.) DIBAL, 2.) NaBH4 / 1.) toluene, -78 deg C, 1.5 h, 2.) MeOH, -30 deg C, 20 min 5: CH2Cl2; pyridine / 1 h / Ambient temperature 6: 80 percent / 2.5 h / Ambient temperature; HMPT 7: 1.) 10percent NaOH / 1.) EtOH, 16 h, reflux, 2.) ether, 0 deg C 8: 100 percent / quinoline, H2 / Lindlar / methanol / 760 Torr 9: 84 percent / pyridine / CH2Cl2 / 1 h / 0 °C 10: 27 g / Et3N / 0.33 h / -20 °C 11: 1.) NaOMe / 1.) MeOH, 0 deg C, 30 min, 1.5 h, r.t., 2.) ether 12: 20 g / CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C 13: DBU / toluene / 0.33 h View Scheme

1: NaI / acetone / 1.5 h / 0 °C 2: 1.) NaOMe / 1.) MeOH, r.t., 30 min, 2.) MeOH, r.t., 4 h, reflux, 1.5 h 3: NaBH4 / methanol / 0.33 h / -55 °C 4: 1.) DIBAL, 2.) NaBH4 / 1.) toluene, -78 deg C, 1.5 h, 2.) MeOH, -30 deg C, 20 min 5: CH2Cl2; pyridine / 1 h / Ambient temperature 6: 80 percent / 2.5 h / Ambient temperature; HMPT 7: 1.) 10percent NaOH / 1.) EtOH, 16 h, reflux, 2.) ether, 0 deg C 8: 100 percent / quinoline, H2 / Lindlar / methanol / 760 Torr 9: 84 percent / pyridine / CH2Cl2 / 1 h / 0 °C 10: 27 g / Et3N / 0.33 h / -20 °C 11: 1.) NaOMe / 1.) MeOH, 0 deg C, 30 min, 1.5 h, r.t., 2.) ether 12: 20 g / CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C 13: DBU / toluene / 0.33 h 14: diethyl ether / 1 h / -78 °C 15: CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C View Scheme