Synthesis of Pterostilbene by Julia Olefination

Abstract

A simple, E-stereoselective route for the synthesis of the biologically active compounds trans-pterostilbene and tetramethoxy stilbene from the readily available starting materials 3,5-dimethoxy benzyl alcohol and 4-hydroxy benzaldehyde was developed using Julia olefination as a key reaction.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resources: Full experimental and spectral details.]

GRAPHICAL ABSTRACT

Keywords:

• 3,5-Dimethoxy benzyl alcohol
• 4-hydroxy benzaldehyde
• Julia olefination
• tetramethoxy stilbene
• trans-pterostilbene

ACKNOWLEDGMENTS

We are grateful for support under the U.S. Department of Agriculture, Agricultural Research Service, Specific Cooperative Agreement No. 58-6408-2-0009. C.A.G. and P.P. are grateful to Jon Parcher for his valuable insights and Bharathi Avula for help with high-resolution mass spectrometry.