Topic: Emulating Terpene Biosynthesis in the Synthesis of Complex Polycyclic Natural Products

Lecturer: Prof. P. Andrew Evans

Time: June 4, 2025, 16:00-17:00, UTC+8

Venue: Room 308, School of Chemistry, Chemical Engineering and Life Sciences, Nanhu Campus

Biography: Professor P. Andrew Evans is the Alfred R. Bader Chair of Organic Chemistry and a Tier 1 Canada Research Chair in Organic and Organometallic Chemistry in the Department of Chemistry at Queen’s University. He is also a Changjiang Scholar at Central South University in China. He received a B.Sc. with honours in Applied Chemistry at Newcastle Polytechnic in 1987 and completed his Ph.D. at the University of Cambridge in 1991 under the supervision of Andrew B. Holmes, FRS. He then pursued postdoctoral research with Philip D. Magnus, FRS, at the University of Texas at Austin as a NATO Postdoctoral Fellow. In 1993, he began his independent career at the University of Delaware, where he was promoted to Professor before moving to Indiana University in 2001. In 2006, he became the Heath Harrison Chair of Organic Chemistry at the University of Liverpool before assuming his current role in 2012. His recent awards include the R. U. Lemieux Award, the Paul G. Gassman Distinguished Service Award, the Harry and Carol Mosher Award, a Changjiang Scholar Award, an ACS Cope Scholar Award and the RSC Pedler Award. He has been actively involved in the ACS Division of Organic Chemistry, serving as a Member-at-Large, Councilor, National Organic Symposium Executive Officer and Division Chair. He currently co-chairs the ACS-DOC Graduate Research Symposium, which he conceived and initiated in 2010 with Gary Molander. Professor Evans has held editorial roles as an Associate Editor for Chemical Communications and Synthesis. He is also the former Editor-in-Chief and current President of Organic Reactions. He has published over 150 papers, articles, reviews, book chapters and monographs and delivered more than 600 plenary and invited lectures.

Abstract: Transition metal-catalyzed higher-order carbocyclizations provide a powerful platform for assembling complex, stereochemically rich polycyclic architectures beyond the reach of classical pericyclic reactions. Our research has advanced this frontier through the development of rhodium-catalyzed [m+n+n] carbocyclizations of carbon- and heteroatom-tethered 1,6-enynes and alkylidene cyclopropanes, forging dense molecular scaffolds from simple precursors with carbon monoxide, alkenes, alkynes, and alkenes as coupling partners. To address long-standing challenges associated with substituted alkenes in 1,6-enynes, we introduced 1,6-chloro-enyne substrates, opening new avenues for several new stereoselective carbocyclization reactions. In parallel, we uncovered new reactivity modes in intramolecular alkylidene cyclopropanes, enabling previously inaccessible bond constructions to access increasingly intricate frameworks. This seminar will highlight the scope, limitations, and synthetic potential of these transformations, emphasizing key mechanistic insights, unexpected reactivity, and the strategic design behind their application to the total synthesis of architecturally complex, bioactive natural products.

Rewritten by: Li Huihui

Edited by: Li Tiantian

Source: School of Chemistry, Chemical Engineering and Life Sciences