A facile, stereoselective, one-pot synthesis of resveratrol derivatives

Vishal Birar, Angela Sheerin, Jana Milkovicova, Richard Faragher, Elizabeth Ostler

Research output: Contribution to journalArticle

Abstract

Background Compounds based on trans-1,2-diphenylethene are the subject of intense interest both for their optical properties and as potential leads for drug discovery, as a consequence of their anticancer, anti-inflammatory and antioxidant properties. Perhaps the best known of these is trans-3,5,4′-trihydroxystilbene (resveratrol), that has been identified as a promising lead in the search for anti-ageing therapeutics. Results We report here a new, convenient, one-pot stereo-selective synthesis of resveratrol and other trans-stilbene derivatives. A wide range of known and novel "Resveralogues" were synthesised by using this simple protocol, including examples with electron donating and electron withdrawing substituents, in uniformly high yield. The structures of all compounds were confirmed by standard methods including 1H and 13C NMR, IR and High Resolution Mass spectroscopy. Conclusions We have established a simple and convenient protocol for resveralogue synthesis. It is readily scalable, and sufficiently robust and simple for ready use in automated synthesis or for library development of resveralogues. This supersedes previously reported synthetic methods that required inert conditions, extensive purification and/or costly reagents.
Original languageEnglish
JournalChemistry Central Journal
Volume9
DOIs
Publication statusPublished - 20 May 2015

Bibliographical note

© 2015 Birar et al.; licensee Springer. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly credited.

Keywords

  • Resveratrol
  • Stilbene
  • Ageing

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