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Back to the Future – Synthetic & Pharmaceutical Applications of Ergot Alkaloids

In spite of considerable advances in Ergot alkaloid chemistry & biology, many frontiers remain, especially with regard to accomplishing the ideal total synthesis, pursuing Ergot analog structure-activity relationship studies and lead development, biosynthetic investigations, and translational and clinical studies. While these investigations pose unique technical and legal challenges, scaffold rearrangement and tailoring of the tetracyclic ergoline system can mitigate unwelcome drug side effects.

We have developed concise synthetic strategies toward Ergot and Clavine alkaloids that allow a rapid assembly of core structures and thus enable iterative SAR investigations, providing us with a significant competitive advantage to pursue medicinal chemistry studies in this field. This seminar will highlight the relevance of (a) synthetic methods enabling efficient synthetic strategies of complex targets, and vice-versa, (b) stereochemical understanding for structure-based design, and (c) scaleability and late-stage functionalization (LSF) for successful small-molecule drug discovery projects.

Peter Wipf‘s PhD studies were conducted at the University of Zürich, Institute of Organic Chemistry, in Switzerland with Prof. Heinz Heimgartner. He has taught at the University of Pittsburgh since 1990 and became Distinguished University Professor in 2004. His research interests include: total synthesis of natural products, synthetic methods for heterocycles and catalysis, photo-flow chemistry and more. In 2023 he was awarded the ACS Award for creative Work in Synthetic Organic Chemistry.

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