Department of Chemistry - Seminar - Assembly-Line Synthesis

Speaker: Professor Varinder K. AGGARWAL

Institution: School of Chemistry, University of Bristol, UK

Hosted By: Professor Yangjian QUAN

Zoom Link: https://hkust.zoom.us/j/95047248788?pwd=RkowN2l4cVFiZFFXZTFpNUpNMFdIZz09

Abstract

Nature has evolved highly sophisticated machinery for organic synthesis, many of which resemble molecular assembly-line processes. So far chemists have been able to apply this type of approach in the synthesis of peptides and oligonucleotides but in these reactions, simple amide (C‒N) or phosphate (P‒O) bonds are created. It is much more difficult to make C‒C bonds but this is central to the discipline of organic synthesis. This difficulty is why organic synthesis is challenging and why robust, iterative or automated methodologies have not yet emerged.

Here, we describe the application of iterative homologation of boronic esters using chiral lithiated carbamates and chloromethyllithium enabling us to grow carbon chains with control over both relative and absolute stereochemistry. Applications of this strategy to the synthesis of natural products will be demonstrated. In addition, the methodology is used to answer fundamental questions about nature and the specific role of methyl substituents in carbon chains. By understanding their role, I will show that molecules can be created with linear or helical conformations or hybrids of the two.

About the speaker

Prof. Varinder K. Aggarwal studied chemistry at Cambridge University and received his Ph.D. in 1986 under the guidance of Dr. Stuart Warren. After postdoctoral studies (1986-1988) under Prof. Gilbert Stork, Columbia University, he returned to the UK as a Lecturer at Bath University. In 1991 he moved to Sheffield University, where he was promoted to Professor in 1997. In 2000 he moved to Bristol University where he holds the Chair in Synthetic Chemistry. He has received numerous awards including RSC Perkin Award 2013; Gilbert Stork Lectureship at University of Wisconsin and Pennsylvania, 2016; Humboldt Research Award 2017; RSC Organic Synthesis Award 2017; Kurt Alder Lectureship 2018, Arthur C. Cope Award 2019, the Yamada-Koga Prize 2019, RS Davy Medal 2019, and the Xingda Lectureship Peking University, 2020. He was elected Fellow of the Royal Society in 2012.