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Absolute Configuration of Dehydrodiconiferyl Alcohol

Nobuhiro Hirai, Masahiko Okamoto, Hiroaki Udagawa, Munehiro Yamamuro, Masayoshi Kato, Koichi Koshimįzu

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Abstract

The absolute configuration of dehydrodiconiferyl alcohol was elucidated by chemical degradation. (+)-Dehydrodiconiferyl alcohol was prepared by optically resolving the recemate with HPLC and degraded to methylsuccinic acid. This methylsuccinic acid was the (R)-(+)-enantiomer, the optical purity of which was confirmed by HPLC after suitable conversion. This result shows that the absolute configuration of C-2 of (+)-dehydrodiconiferyl alcohol was S. H-2 and H-3 of (+)-dehydrodiconiferyl alcohol are trans, so the absolute configuration of C-3 must be R. Thus, (+)-dehydrodiconiferyl alcohol was 2S and 3R, and the (−)-enantiomer was 2R and 3S. The absolute configuration of natural glucosides of dehydrodiconiferyl alcohol was also elucidated.

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What this paper is about

The absolute configuration of dehydrodiconiferyl alcohol was elucidated by chemical degradation. (+)-Dehydrodiconiferyl alcohol was prepared by optically resolving the recemate with HPLC and degraded to methylsuccinic acid. This methylsuccinic acid was the (R)-(+)-enantiomer, the optical purity of which was confirmed by HPLC after suitable conversion. This result shows that the absolute configuration of C-2 of (+)-dehydrodiconiferyl alcohol was S. H-2 and H-3 of (+)-dehydrodiconiferyl alcohol are trans, so the absolute configuration of C-3 must be R. Thus, (+)-dehydrodiconiferyl alcohol was 2S and 3R, and the (−)-enantiomer was 2R and 3S. The absolute configuration of natural glucosides of dehydrodiconiferyl alcohol was also elucidated.

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Available abstract

The absolute configuration of dehydrodiconiferyl alcohol was elucidated by chemical degradation. (+)-Dehydrodiconiferyl alcohol was prepared by optically resolving the recemate with HPLC and degraded to methylsuccinic acid. This methylsuccinic acid was the (R)-(+)-enantiomer, the optical purity of which was confirmed by HPLC after suitable conversion. This result shows that the absolute configuration of C-2 of (+)-dehydrodiconiferyl alcohol was S. H-2 and H-3 of (+)-dehydrodiconiferyl alcohol are trans, so the absolute configuration of C-3 must be R. Thus, (+)-dehydrodiconiferyl alcohol was 2S and 3R, and the (−)-enantiomer was 2R and 3S. The absolute configuration of natural glucosides of dehydrodiconiferyl alcohol was also elucidated.

Key concepts: Absolute configuration, Alcohol, Enantiomer, Chemistry, High-performance liquid chromatography, Absolute (philosophy), Ethanol, Stereochemistry

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