Resveratrol (3,4',5-trihydroxystilbene) is produced by plants in response to stress and is found in plant-derived foods such as red grapes and red wine. Resveratrol has been investigated for several potential therapeutic effects although the exact mechanism of action is not yet known. Both cis-resveratrol and trans-resveratrol occur naturally. The purpose of this study was to develop an inexpensive and efficient method to prepare a library of analogs of cis- and trans-resveratrol that can be used in future experiments to investigate the relationship between the chemical structure and biological activity of resveratrol. This report details the synthetic steps used to prepare multi-gram quantities of these novel resveratrol analogs. The Wittig-Horner reaction and McMurry coupling were used to prepare exclusively the trans-isomers. The Perkin reaction followed by decarboxylation produced pure cis-isomers. Products were characterized by FTIR, 1H-NMR, COSY, 13C-NMR, DEPT and HETCOR spectroscopy.

Stereospecific syntheses of novel analogs of <i>cis</i>- and <i>trans</i>-resveratrol

245th National Meeting (2013)

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Stereospecific syntheses of novel analogs of cis- and trans-resveratrol