Lecture

Total Synthesis: Pattern Recognition and Key Motifs

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In course

CH-438: Total synthesis of natural products

Complex polycyclic natural products are chosen to illustrate the evolution of the state-of-the-art of the field, the interplay between strategy and new reactions as well as the importance of implementing multi-bond forming processes in a synthesis. ...

Description

This lecture delves into the concept of pattern recognition in total synthesis, emphasizing the discovery of substructural motifs to guide the synthesis process. Key motifs like 3-Acyl proline are explored through examples such as Oppolzer's synthesis of Longifolene and Qin's synthesis of Minfiensine. The lecture also covers the synthesis of Actinophyllic acid, highlighting important steps like the Aza-Cope/Mannich sequence and conformation analysis. Various synthesis pathways are discussed, showcasing the intricate strategies employed in total synthesis.

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Instructor

Jieping Zhu

Teaching & PhD PhD Students Morgane Elodie Marie Delattre, Paul Jean Gri, Clément Paul Adrien Rols, Yun Hao Shawn Teh Past EPFL PhD Students Jean-Baptiste Gualtierotti, Ala Bunescu, Thomas Buyck, Olivier Wagnières, Minh Tu Ha, Dylan Jean Robert Dagoneau, Antonin François Roland Clemenceau, Cyril Piemontesi, Nicolas David Gaeng, Mathias Mamboury, Raphaël Beltran, Balázs Budai, Teerawat Songsichan, Alexandre Julien Florent Leclair, Bastien Delayre, Rémi Julien Sylvain Andres, Dina Boyarskaya, Rémi Lavernhe,

Official source

Related concepts (19)

Total synthesis

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest.

Metabolic pathway

In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical reactions catalyzed by enzymes. In most cases of a metabolic pathway, the product of one enzyme acts as the substrate for the next. However, side products are considered waste and removed from the cell. These enzymes often require dietary minerals, vitamins, and other cofactors to function.

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior.

Polycyclic compound

In the field of organic chemistry, a polycyclic compound is an organic compound featuring several closed rings of atoms, primarily carbon. These ring substructures include cycloalkanes, aromatics, and other ring types. They come in sizes of three atoms and upward, and in combinations of linkages that include tethering (such as in biaryls), fusing (edge-to-edge, such as in anthracene and steroids), links via a single atom (such as in spiro compounds), bridged compounds, and longifolene.

Organic compound

In chemistry, many authors consider an organic compound to be any chemical compound that contains carbon-hydrogen or carbon-carbon bonds, however, some authors consider an organic compound to be any chemical compound that contains carbon. The definition of "organic" versus "inorganic" varies from author to author, and is a topic of debate. For example, methane () is considered organic, but whether some other carbon-containing compounds are organic or inorganic varies from author to author, for example halides of carbon without carbon-hydrogen and carbon-carbon bonds (e.

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