Functional Group Migration Cascades and Total Synthesis of Complex Meroterpenoids

Please join Yale Chemistry for the Sigma Aldrich Lecture in organic chemistry with Prof. Martin Tomanik, Assistant Professor of Chemistry, New York University.

Abstract: Within the realm of chemoselective manipulations, site-selective functional group translocation via C–H functionalization presents an exciting opportunity to unlock new synthetic disconnections. I will highlight our development of a radical-triggered annulative alkene transposition reaction, as well as a palladium-catalyzed annulation enabled by a previously inaccessible through-space alkyl-to-alkyl palladium migration mechanism. In the second part, I will discuss our synthetic strategy toward the highly oxidized meroterpenoid talaromyolide D. Our approach leverages efficient C–H disconnection logic to elaborate the polycyclic core of the target, along with several highly diastereoselective transformations, including an electrocatalytic sp²–sp³ cross-coupling.

Bio: Martin was born and raised in the small town of Prerov, Czech Republic. He attended Dartmouth College for his undergraduate studies and graduated in 2015. In 2016, he began his doctoral studies at Yale University under the supervision of Prof. Seth Herzon. While at Yale, Martin completed total syntheses of the dihydro-β-agarofuran sesquiterpenoid (–)-euonyminol and the genotoxic pimarane diterpene (–)-myrocin G. In the summer of 2021, Martin moved to San Diego to pursue post-doctoral studies in the laboratory of Prof. Jin-Quan Yu at The Scripps Research Institute. While at Scripps, Martin focused broadly on the discovery of carboxylic acid and native amide-directed C–H activation reactions. In 2023, Martin joined the faculty at New York University as an assistant professor in the department of chemistry. For more information on Prof. Tomanik's research: Home | The Tomanik Lab at NYU

Hosted by Prof. Seth Herzon.