Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

(E)-3-(β-d-Glucopyranosyloxy)-4′,5-dihydroxystilbene (resveratrol 3-β-d-glucoside, piceid), (Z)-2′,3′-dihydroxy-3,4,4′,5-tetramethoxystilbene (combretastatin A-1), (Z)-3′-hydroxy-3,4,4′,5-tetramethoxystilbene (combretastatin A-4), (Z)-2′-hydroxy-3,4,4′,5-tetramethoxystilbene (combretastatin iso-A-4), α,β-dihydro-2′,3′-dihydroxy-3,4,4′,5-tetramethoxystilbene (combretastatin B-1), the corresponding glucosides, and related compounds have been synthesized via Wittig reactions followed by glucosylation under phase-transfer catalysis. Most of the compounds synthesized have been tested with respect to biological activity (cytostatic, cytotoxic, antimitotic, neurotoxic, antiplatelet aggregation activity).