Resveratrol, a natural product that is made as a stress response by several plants, has been highly popularized in recent years because of some observed health benefits in age-related diseases. We became interested in resveratrol analogues through a collaboration to use these compounds in an attempt to induce osteogenesis in mesenchymal stem cells (MSCs) and quickly discovered that these stilbene derivatives are much more difficult and time-consuming to synthesize than it would seem. Facile synthesis of these invaluable compounds is absent in the literature—most methods require several steps from commercial materials and/or conditions that are found only in specialized organic synthesis labs. We are working on addressing these issues through a 1-pot tandem Sonogashira coupling reaction to build asymmetric alkynes, which can then be selectively reduced to the desired <i>cis</i> or <i>trans</i> stilbene. In order to address both concerns, we have devised a way to exclude copper from the system, thus allowing the synthesis to be done under aerobic conditions with no special apparatus. Our progress toward a broadly applicable method will be discussed in the context of novel resveratrol analogue synthesis.

Facile synthesis of resveratrol analogues and inducing osteogenesis in mesenchymal stem cells

253rd National Meeting (2017)

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