Lecture

Total Synthesis: Hirsutellone B

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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 total synthesis of Hirsutellone B, focusing on the strategies and reactions used by the instructor, including Nicolaou's approach, intramolecular D-A reactions, and the formation of macrocycles. Key tactics such as organocatalytic enantioselective epoxidation and Barton etherification are discussed, leading to the final product with a 1.2% overall yield.

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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 (16)

Catenane

In macromolecular chemistry, a catenane () is a mechanically interlocked molecular architecture consisting of two or more interlocked macrocycles, i.e. a molecule containing two or more intertwined rings. The interlocked rings cannot be separated without breaking the covalent bonds of the macrocycles. They are conceptually related to other mechanically interlocked molecular architectures, such as rotaxanes, molecular knots or molecular Borromean rings.

Rotaxane

A rotaxane () is a mechanically interlocked molecular architecture consisting of a dumbbell-shaped molecule which is threaded through a macrocycle (see graphical representation). The two components of a rotaxane are kinetically trapped since the ends of the dumbbell (often called stoppers) are larger than the internal diameter of the ring and prevent dissociation (unthreading) of the components since this would require significant distortion of the covalent bonds.

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.

Aldol reaction

The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.

Transfer hydrogenation

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular . It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis.

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