Synthesis of Pterostilbene by Julia-olefination

Polyhydroxy stilbenes such as resveratrol and pterostilbene have been reported to exhibit a range of biological activities including anti-cancer, induction of peroxisome proliferator activated receptor-alpha (PPAR-γ)[1], antioxidant, anti-inflammatory and other potential health benefits [2]. Pterostilbene is found in nature in a variety of grapes and berries as well as plants commonly used in traditional folk medicine. Due to its perceived health benefits, significant interest in synthesis of pterostilbene has been generated in recent years by using Wittig, Wittig-Horner [1], Perkin reaction [3] and transition metal catalyzed reactions [4]. Here we report a simple, economical method for the preparation pterostilbene using Julia olefination as a key reaction, and the details of the synthetic results will be presented.

R₁,R₂=H; ResveratrolR₁,R₂=Me; Pterostilbene

Acknowledgements: NCNPR, University of Mississippi, United States Department of Agriculture, Agricultural Research Service, Specific Cooperative Agreement No. 58–6408–2-0009. References: [1] Rimando, et al. (2008) Bioorg & Med Chem, 16: 3800. [2] Joshi VK, Devi MP (2009) Proceedings of the National Academy of Sciences, India, Section B: Biological Sciences 79(3): 212–226. [3] Arun KS, et al. (2007) Tetrahedron 63: 11070. [4] Moro AV, Cardoso FS, et al. (2008) Tet Lett 49(39): 5668–5671.