1: methyl 8-(diethylphosphono)-9-oxodec-5(Z)-enoate With sodium hydride in tetrahydrofuran T=-5°C; 2 h; 2: glyoxal 1,1-dimethyl acetal in tetrahydrofuran T=-78 - -25°C;

chromium(VI) oxide; Celite in pyridine; dichloromethane T=0°C; 0.166667 h; Yield given;

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

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

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

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

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

1: 100 percent / quinoline, H2 / Lindlar / methanol / 760 Torr 2: 84 percent / pyridine / CH2Cl2 / 1 h / 0 °C 3: 27 g / Et3N / 0.33 h / -20 °C 4: 1.) NaOMe / 1.) MeOH, 0 deg C, 30 min, 1.5 h, r.t., 2.) ether 5: 20 g / CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C 6: DBU / toluene / 0.33 h 7: diethyl ether / 1 h / -78 °C 8: CrO3, Celite / CH2Cl2; pyridine / 0.17 h / 0 °C View Scheme

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