Mediaspace scheduled maintenance: Aug 25, 2026 07:00 - 12:00 AM. During this time, videos will be temporarily unavailable. Check status updates.

Lecture

Enantioselective Synthesis: Phalarine

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.

Instructor

Jieping Zhu

Official source

Related concepts (32)

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.

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.

Decarboxylation

Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in photosynthesis, is called carboxylation, the addition of CO2 to a compound. Enzymes that catalyze decarboxylations are called decarboxylases or, the more formal term, carboxy-lyases (EC number 4.1.1).

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.

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

Related lectures (32)

Asymmetric Reactions in Organic Chemistry

Delves into asymmetric reactions in organic chemistry, highlighting mechanisms, catalysts, and selectivity.

Catalytic Cycloadditions: Enantioselective Strategies

Explores catalytic cycloadditions and enantioselective strategies, including dynamic kinetic transformations and asymmetric rearrangements.

Asymmetric catalysis

Explores asymmetric catalysis, umpolung, and selectivity models in various catalytic reactions, offering insights into the future of this field.

Catalytic Functionalization of Olefins

Explores catalytic reactions for olefin functionalization, covering asymmetric allylation, hydrogenation, isomerization, hydroamination, hydroboration, and radical reactions.

Enantioselective C-H Activation