η6-Arene–tricarbonylchromium complexes in the syntheses of trans-resveratrol and pinostilbene

Abstract

New syntheses of trans-resveratrol (trans-3,5,4'-trihydroxystilbene) and pinostilbene (trans-3,4'-dihydroxy-5-methoxystilbene) via nucleophilic demethylation of trimethoxystilbene were performed, whereby trans-3,5,4'-trimethoxystilbene was obtained through facilitated benzylic deprotonation of an η⁶-benzene-Cr(CO)₃ derivative and subsequent coupling with para-anisaldehyde in an aldol-type or Wittig–Horner reaction.