aluminum isopropoxide in cyclohexane; toluene 0.166667 h; Heating;

(microbiological transformation);

Cephalosporium aphidicola in ethanol; dimethyl sulfoxide 192 h;

sodium tetrahydroborate in ethanol

1: 95 percent / pyridine, 4-(dimethylamino)pyridine / 1.75 h / Ambient temperature 2: 96 percent / NaBH4 / ethanol; dioxane / 1.5 h / Ambient temperature 3: 99 percent / pyridinium p-toluenesulfonate / tetrahydrofuran / 14 h / Ambient temperature 4: 93 percent / KOH / methanol / 9.5 h / Ambient temperature 5: Collins reagent / CH2Cl2 / 0.5 h / Ambient temperature 6: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / CH2Cl2; methanol / 0.33 h / Ambient temperature 7: 93 percent / collidine / benzene / 0.67 h / 0 °C 8: 40 percent / KOH, 30percent aq. HOOH / CH2Cl2; methanol / 4 h / 4 °C View Scheme

Multi-step reaction with 7 steps 1: 95 percent / pyridine, 4-(dimethylamino)pyridine / 1.75 h / Ambient temperature2: 96 percent / NaBH4 / ethanol; dioxane / 1.5 h / Ambient temperature3: 99 percent / pyridinium p-toluenesulfonate / tetrahydrofuran / 14 h / Ambient temperature4: 93 percent / KOH / methanol / 9.5 h / Ambient temperature5: Collins reagent / CH2Cl2 / 0.5 h / Ambient temperature6: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / CH2Cl2; methanol / 0.33 h / Ambient temperature7: 93 percent / collidine / benzene / 0.67 h / 0 °C  

Multi-step reaction with 8 steps 1: 95 percent / pyridine, 4-(dimethylamino)pyridine / 1.75 h / Ambient temperature2: 96 percent / NaBH4 / ethanol; dioxane / 1.5 h / Ambient temperature3: 99 percent / pyridinium p-toluenesulfonate / tetrahydrofuran / 14 h / Ambient temperature4: 93 percent / KOH / methanol / 9.5 h / Ambient temperature5: Collins reagent / CH2Cl2 / 0.5 h / Ambient temperature6: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / CH2Cl2; methanol / 0.33 h / Ambient temperature7: 93 percent / collidine / benzene / 0.67 h / 0 °C8: 15 percent / KOH, 30percent aq. HOOH / CH2Cl2; methanol / 4 h / 4 °C