Domino Primary Alcohol Oxidation-Wittig Reaction: Total Synthesis of ABT-418 and (E)-4-Oxonon-2-enoic Acid

Abstract

Domino oxidation of primary alcohols to α,β-unsaturated compounds using the combination of PCC-NaOAc and stabilized Wittig reagent and its application towards total synthesis of ABT-418 and 4-oxonon-2-enoic acid is described.

Keywords

primary alcohols - oxidation - PCC - olefination - domino reaction

References

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12

Enantiomeric purity of the products ethyl (2S)-2-[(1E)-3-oxobut-1-enyl]pyrrolidine-1-carboxylate, 3-methyl-5-(carboethoxy)pyrrolidinyl isoxazole, 3-methyl-5-[1-methyl-2-(S)-pyrrolidinyl] isoxazole (ABT-418) were determined on chiral AD-column as reported in an earlier synthesis (see reference 5b).