1: 1.) DIBAL, 2.) NaBH4 / 1.) toluene, -78 deg C, 1.5 h, 2.) MeOH, -30 deg C, 20 min 2: CH2Cl2; pyridine / 1 h / Ambient temperature View Scheme

1: 1.) DIBAL, 2.) NaBH4 / 1.) toluene, -78 deg C, 1.5 h, 2.) MeOH, -30 deg C, 20 min 2: CH2Cl2; pyridine / 1 h / Ambient temperature 3: 80 percent / 2.5 h / Ambient temperature; HMPT View Scheme

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

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