Dehydroconiferyl alcohol

A stereocontrolled synthesis of the biologically active neolignan (+)-dehydrodiconiferyl alcohol, which was isolated from several Taxus species, was achieved via Evans asymmetric aldol condensation [58] using ferulic acid amide derived from D-phenylalanine. The reaction steps are shown in Fig. 9. This stereocontrolled reaction is also useful for preparing the enantiomer of (+)-dehydroconiferyl alcohol using chiral auxiliary oxazolidinone prepared from L-phenylalanine. This reaction also enables the syntheses of other natural products that possess the same phenylcoumaran framework. 

Glucosides of dehydroconiferyl alcohols (21-23) (O Scheme 8) and the respective 2,3-epi-mers are growth factors isolated from transformed Vmca rosea tumor cells [24]. These compounds are not fragments of cell walls, but are produced directly from coniferyl alcohol [25]. Nonglycosylated derivatives do not have the cytokinine activity. 

Coniferyl alcohol is dehydrogenated in vivo under the influence of the enzyme laccase. The dehydroconiferyl alcohol free radical produced can react further via three mesomorphic forms ... 

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