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Title: Synthesis of trans-resveratrol using modified Julia olefination route
Authors: Shenvi, Suvarna
Shivanna, Shivaprakash
Reddy, G Chandrasekara
Keywords: Julia olefination;Stilbenes;Benzothiazol-2-yl sulfone;p-anisaldehyde;trans-resveratrol;Veratrum album
Issue Date: Aug-2016
Publisher: NISCAIR-CSIR, India
Abstract: Bioactive hydroxystilbinoid−trans-resveratrol [(E)-3,5,4ʹ-trihydroxy stilbene, 1] has been synthesized by modified Julia olefination method. The reaction between corresponding carbanion of benzothiazol-2-yl sulfone derivative and p-anisaldehyde dimethyl acetal with sodium hydride as a base, affords mainly cis-3,5,4ʹ-trimethoxystilbene 10b with minor quantity of trans-isomer. Both the isomers have been separated in pure form and confirmed by their NMR spectral data. Demethylation of cis-3,5,4ʹ-trimethoxystilbene either with AlCl3/pyridine or AlCl3/triethylamine results in the formation of trans-resveratrol.
Page(s): 1035-1038
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.55B(08) [August 2016]

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