Radical-Based Approach for Synthesis of Complex Natural Products

Event time: 
March 8, 2023 - 4:00pm to 5:30pm
Sterling Chemistry Laboratory (SCL) See map
Event description: 

Location: SCL 160

Join Yale Chemistry for a Jerome A. Berson Lecture in Physical Organic Chemistry with Masayuki Inoue, Professor, University of Tokyo.

Abstract: Natural products with a high ratio of sp3-hybridized atoms and oxygen-substituted stereogenic centers represent privileged structures for the development of pharmaceuticals and chemical probes. The multiple oxygen functionalities of these natural products endow their potent and selective biological activities, although they significantly heighten the challenge of their chemical assemblies.1 We focused on developing efficient strategies for the total syntheses of this biologically and chemically important class of molecules. Specifically, we have designed and devised radical-based strategies for assembling highly oxygenated natural products.2,3 In this lecture, we report the development of the radical coupling reactions and the synthetic routes to resiniferatoxin (1),4,5 hikizimycin (2),6 and euonymine (3)7 by applying the radical chemistry.

About: The goal of the Inoue research program is efficient, practical and flexible syntheses of gigantic natural molecules, which include highly oxygenated polycyclic natural products as well as ion channel-forming peptides. At the core of this research program is the development of new strategies for assembling architecturally complex natural products in a concise fashion. These synthetic developments would enable unified synthesis of new artificial analogs by modification of natural products templates. The new synthetic methods for the natural products and the synthetic analogs will allow us to tailor and enhance their drug like properties, to gain control over diverse signal transductions thereby offering new research methods for the study of life science.

This seminar is generously sponsored by the Mrs. Hepsa Ely Silliman Memorial Fund