The Udho Parsini Diwan Award rewards the graduate student in the McGill Chemistry program who has written the best research article published the year before. Here is how Anna Alberston presents her winning article.
Scientists have often looked to nature for novel pharmaceuticals, including in the stems, leaves, and bark of plants and trees. One such class of natural products are the lignans, which have found numerous applications in the treatment of cancer, viruses and inflammation. In spite of their demonstrated utility, the synthesis of lignan natural products is still challenging, and a general methodology that can access the family’s complete structural diversity has not been described.
In our work, published recently in ACIE, we addressed the challenge of synthesizing lignan natural products by once again turning to nature for inspiration. In summary, we have developed a route to the key branch point of lignan biosynthesis, from which a dizzying array of downstream products are produced. More specifically, we have demonstrated that a key diaryl-cyclobutane, easily accessed by a photochemical [2+2] of readily available starting materials, can be oxidatively ring-opened to access the natural products tanegool and pinoresinol. We are currently extending this approach to other members of the lignan family, in an effort to develop a unified synthesis.