Pahutoxin: Synthesis and Determination of Its Absolute Configuration

Abstract

Optically pure pahutoxin and its antipode were synthesized from (S)- and (R)-3-hydroxyhexadecanoic acids, which were obtained by the enantio-differentiating hydrogenation of methyl 3-oxohexadecanoate over asymmetrically modified Raney nickel catalyst. By an optical correlation with synthetic materials, dextrorotatory natural pahutoxin was determined to be of (S)-configuration.