chromium(VI) oxide; sulfuric acid T=50°C; 1 h;

potassium hydroxide in ethanol 0.5 h; Heating;

pyrrolidine; pyridine in tetrahydrofuran T=0 - 20°C; Doebner-Knoevenagel condensation reaction; Inert atmosphere; stereoselective reaction;

(i) NaOH, MeOH, (ii) NaBH4, MeOH; Multistep reaction;

1: (i) Al, HgCl2, I2, THF, (ii) /BRN= 1905666/ 2: HgSO4*2HgO, H2SO4 / dioxane / Heating 3: H2 / Pd-CaCO3 / methanol 4: Na2CO3 / dioxane / 150 °C 5: KBH4 / methanol View Scheme

1: Heating 2: (i) Al, HgCl2, I2, THF, (ii) /BRN= 1905666/ 3: HgSO4*2HgO, H2SO4 / dioxane / Heating 4: H2 / Pd-CaCO3 / methanol 5: Na2CO3 / dioxane / 150 °C 6: KBH4 / methanol View Scheme

1: 44 percent / 80percent NaH, 1,3-propanediamine / 16 h / 60 °C 2: p-toluenesulfonic acid monohydrate / 0.67 h / Ambient temperature 3: 1.) 1.55M nBuLi / 1.) THF, hexane, -78 deg C, 5 min; -30 deg C, 5 min, 2.) THF, hexane, -78 deg C, 15 min; r.t., 20 min 4: p-toluenesulfonic acid monohydrate / methanol / 0.08 h / Heating 5: 99 percent / H2 / 5percent Pd/BaSO4 / pyridine; quinoline / 0.67 h / 750.06 Torr 6: 72 percent / diphenyldisulfide / cyclohexane / 1.83 h / Irradiation 7: 99 percent / 2N KOH / ethanol / 0.5 h / Heating View Scheme

1: 1.) 1.55M nBuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, HMPT, -20 deg C, 10 min; r.t., 16 h 2: 44 percent / 80percent NaH, 1,3-propanediamine / 16 h / 60 °C 3: p-toluenesulfonic acid monohydrate / 0.67 h / Ambient temperature 4: 1.) 1.55M nBuLi / 1.) THF, hexane, -78 deg C, 5 min; -30 deg C, 5 min, 2.) THF, hexane, -78 deg C, 15 min; r.t., 20 min 5: p-toluenesulfonic acid monohydrate / methanol / 0.08 h / Heating 6: 99 percent / H2 / 5percent Pd/BaSO4 / pyridine; quinoline / 0.67 h / 750.06 Torr 7: 72 percent / diphenyldisulfide / cyclohexane / 1.83 h / Irradiation 8: 99 percent / 2N KOH / ethanol / 0.5 h / Heating View Scheme

1: p-toluenesulfonic acid monohydrate / 0.67 h / Ambient temperature 2: 1.) 1.55M nBuLi / 1.) THF, hexane, -78 deg C, 5 min; -30 deg C, 5 min, 2.) THF, hexane, -78 deg C, 15 min; r.t., 20 min 3: p-toluenesulfonic acid monohydrate / methanol / 0.08 h / Heating 4: 99 percent / H2 / 5percent Pd/BaSO4 / pyridine; quinoline / 0.67 h / 750.06 Torr 5: 72 percent / diphenyldisulfide / cyclohexane / 1.83 h / Irradiation 6: 99 percent / 2N KOH / ethanol / 0.5 h / Heating View Scheme

1: 99 percent / H2 / 5percent Pd/BaSO4 / pyridine; quinoline / 0.67 h / 750.06 Torr 2: 72 percent / diphenyldisulfide / cyclohexane / 1.83 h / Irradiation 3: 99 percent / 2N KOH / ethanol / 0.5 h / Heating View Scheme