Absolute Configuration of Dehydrodiconiferyl Alcohol

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.