Resveratrol is a naturally occuring compound released from certain plants as a stress response. Recently, it has been studied extensively due to its potential anti-cancer properties. A fast and efficient synthetic route is necessary to further resveratrol’s study. Our proposed palladium-catalyzed Sonogashira coupling reaction provides an effective way to produce these compounds because it requires fewer steps and has the potential to give, after selective reduction, a single desired diastereomer of the stilbene product. In the absence of copper, we can perform the reactions in the presence of oxygen, but they are slow without alkyne activation. To combat this, we are employing a gold cocatalyst. Testing various gold compounds, we hope to optimize the catalytic effeciency of Sonogashira coupling for solvent-free, tandem reactions in the ball-mill. In addition, we are developing a method to stereoselectively reduce the resulting diaryl alkyne using the same catalytic system, for eventual in situ application. Our results will be discussed in detail.

Synthesis of resveratrol analogues for cancer research via sonogashira coupling and stereoselective reduction by green methods

2019 Spring National Meeting

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