Lecture

Enantioselective Synthesis: Phalarine

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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 covers the attempted enantioselective synthesis of Phalarine, including the use of Suzuki-Miyaura coupling, formaline reactions, and decarboxylation. It also discusses the total synthesis of Phalarine and Aspidophytine, highlighting key reactions and strategies.

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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 (31)

Suzuki reaction

The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of palladium-catalyzed cross-couplings in organic synthesis. This reaction is also known as the Suzuki–Miyaura reaction or simply as the Suzuki coupling.

Oxidative decarboxylation

Oxidative decarboxylation is a decarboxylation reaction caused by oxidation. Most are accompanied by α- Ketoglutarate α- Decarboxylation caused by dehydrogenation of hydroxyl carboxylic acids such as carbonyl carboxylic acid, malic acid, isocitric acid, etc. Pyruvate catalytic reaction catalyzed by pyruvate dehydrogenase system is a special decarboxylation method, namely oxidative decarboxylation, which is different from the common decarboxylation reaction, namely common decarboxylation.

Rearrangement reaction

In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular. In the example below, the substituent R moves from carbon atom 1 to carbon atom 2: Intermolecular rearrangements also take place.

Asymmetric induction

Asymmetric induction (also enantioinduction) describes the preferential formation in a chemical reaction of one enantiomer or diastereoisomer over the other as a result of the influence of a chiral feature present in the substrate, reagent, catalyst or environment. Asymmetric induction is a key element in asymmetric synthesis. Asymmetric induction was introduced by Hermann Emil Fischer based on his work on carbohydrates. Several types of induction exist.

Vinyl halide

In organic chemistry, a vinyl halide is a compound with the formula CH2=CHX (X = halide). The term vinyl is often used to describe any alkenyl group. For this reason, alkenyl halides with the formula RCH=CHX are sometimes called vinyl halides. From the perspective of applications, the dominant member of this class of compounds is vinyl chloride, which is produced on the scale of millions of tons per year as a precursor to polyvinyl chloride. Polyvinyl fluoride is another commercial product.

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