Lecture

Total Synthesis: MacMillan's Approach to Minfiensine

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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 (+)-Minfiensine using MacMillan's approach, including the retro analysis, access to tetracycle, end game strategy, and the construction of the tetracyclic pyrroloindoline unit. It also explores the reactivity of indole, the attempted biomimetic synthesis of Phalarine, and the retro synthesis of Phalarine. The lecture delves into the mechanisms involved in the formation of tetrahydrocarbazole and the challenges faced in the synthesis of spiroindolenine. It concludes with the validation of the Wagner-Meerwein rearrangement hypothesis and the attempted enantioselective synthesis of Phalarine.

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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,

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Related concepts (30)

Strategy game

A strategy game or strategic game is a game (e.g. a board game) in which the players' uncoerced, and often autonomous, decision-making skills have a high significance in determining the outcome. Almost all strategy games require internal decision tree-style thinking, and typically very high situational awareness. Strategy games are also seen as a descendant of war games, and define strategy in terms of the context of war, but this is more partial.

Abstract strategy game

Abstract strategy games in contrast to strategy games in general usually have no or minimal narrative theme, outcomes determined only by player choice (with no randomness), and all players have perfect information about the game. For example, Go is a pure abstract strategy game since it fulfills all three criteria; chess and related games are nearly so but feature a recognizable theme of ancient warfare; and Stratego is borderline since it is deterministic, loosely based on 19th-century Napoleonic warfare, and features concealed information.

Peptide synthesis

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus).

Solid-phase synthesis

In chemistry, solid-phase synthesis is a method in which molecules are covalently bound on a solid support material and synthesised step-by-step in a single reaction vessel utilising selective protecting group chemistry. Benefits compared with normal synthesis in a liquid state include: High efficiency and throughput Increased simplicity and speed The reaction can be driven to completion and high yields through the use of excess reagent. In this method, building blocks are protected at all reactive functional groups.

Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. For example, lithium aluminium hydride is a highly reactive but useful reagent capable of reducing esters to alcohols.

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