Publications associées à Wender Taxol total synthesis

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent

Dina Boyarskaya

Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...

EPFL2023

Asymmetric Total Synthesis of Indole Alkaloids (+)-Condyfoline, (-)-Tubifoline, (+)-Dasycarpidone and (+)-Uleine

Bastien Delayre

The development of a titanium(III)-mediated cascade electrocyclisation/rearrangement for the enantioselective total synthesis of indole alkaloids (+)-condyfoline and (-)-tubifoline serve as the basis of the first chapter of this thesis. An introduction wil ...

EPFL2022

Enantioselective Total Synthesis of (+)-Alstilobanine C, (+)-Undulifoline, and (-)-Alpneumine H

Qian Wang, Jieping Zhu, Cyril Piemontesi, Guang Li, Nicolas David Gaeng

We report herein the enantioselective total synthesis of three monoterpene indole alkaloids, namely, (+)-alstilobanine C, (+)-undulifoline, and (-)-alpneumine H. The key features of our synthesis include: a) introduction of chirality via enantioselective d ...

Wiley-VCH Verlag GmbH2021

Alkynyl triazenes enable divergent syntheses of 2-pyrones

Kay Severin, Nicolai Cramer, Carl Thomas Bormann, Jin Fay Tan

The 2-pyrone motif occurs frequently in bioactive natural products and is appreciated as synthetic intermediates. However, only few methods allow for diversifying functional group modifications on this relevant heterocycle. The distinct properties of 1-alk ...

2021

Total Synthesis of Alstolactine A & Synthetic Studies Towards Members of Akuammiline Alkaloids

Raphaël Beltran

The work presented in this thesis focuses on the synthesis of monoterpene indole alkaloids. The first part describes the development of a general methodology to provide an enantioenriched platform, useful for the convergent synthesis of Akuammiline alkalo ...

EPFL2019

Indole Alkaloids, Macrocycles and Heterocycles : Interplay between Methodological Development and Total Synthesis

Cyril Piemontesi

An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...

EPFL2018

Total Synthesis of Alstilobanine C, Undulifoline and Alstilobanine B

Nicolas David Gaeng

The total synthesis of pentacyclic monoterpene indole alkaloids is the focus of this thesis. Total syntheses of (±)-alstilobanine C, (±)-undulifoline and (±)-alstilobanine B, three natural products from the Ulean family of alkaloids, were accomplished. The ...

EPFL2018

Lewis acid Catalyzed Annulations of Donor-Acceptor Aminocyclopropanes and Aminocyclobutanes

Sophie Lucie Racine

Organic molecules are indispensable have greatly contributed to the confort of our modern life. Nevertheless, humanity is facing now new challenges such as environmental issues and emerging drug resistances. In order to solve these major concerns, chemists ...

EPFL2016

Total Synthesis of Aspidosperma Family Indole Alkaloids through the iORC Domino Process

Olivier Wagnières

This thesis describes a unified strategy for the synthesis of monoterpene indole alkaloids of the Aspidosperma family. These syntheses feature two key steps: (1) a palladiumcatalyzed decarboxylative vinylation that provides quick access to cyclopentene int ...

EPFL2015

Isocyanoacetates as Synthetic Platform Towards Natural Products and Biologically Relevant Scaffolds

Thomas Bertrand Pascal Marie Buyck

My PhD work started with the development of a racemic access to trigonoliimine B, an hexacyclic alkaloid isolated in 2010. After having explored different strategies, we reported a 7-step synthesis of this natural product. This synthesis features a challen ...

EPFL2014

Synthesis, Biological Evaluation and Docking Studies of Casuarine Analogues: Effects of Structural Modifications at Ring B on Inhibitory Activity Towards Glucoamylase

Pierre Vogel, Claudia Bello

We report the total synthesis of a series of pyrrolizidine analogues of casuarine (1) and their 6-O-alpha-glucoside derivatives. The synthetic strategy is based on a totally regio- and stereoselective 1,3-dipolar cycloaddition of suitably substituted alken ...

2010

Access to long-chain polyketides by double-elongation reactions : the AB and CD spiroacetals of the spongistatins

Christopher Flowers

Due to the spongistatins' fascinating and complex molecular architectures, and their important biological activities, these marine macrolides have been the subject of intensive efforts directed towards their total synthesis. As an attractive alternative to ...

EPFL2010

Cyclization and Cycloaddition Reactions of Cyclopropyl Carbonyls and Imines

Jérôme Waser, Filippo De Simone

Activated cyclopropanes, such as vinyl and carbonyl cyclopropanes, are useful building blocks in organic chemistry due to their exceptional reactivity. This review focuses on the use of cyclopropyl carbonyls and imines in cyclization and cycloaddition reac ...

Georg Thieme Verlag2009

Preparation and synthetic applications of 8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives

Pierre Vogel, Sandrine Gerber, Sylvain Favre

The development of efficient routes to multi gram quantities of chiral synthons is a key issue in total synthesis of natural products and analogues. The conformationally defined and rigid 8-oxabicyclo[3.2.1]oct-6-en-3-one template appears as an appealing s ...

2008

Biomimetic Total Synthesis and Antimicrobial Evaluation of Anachelin H

Karl Gademann

The first biomimetic total synthesis of the iron chelator anachelin H isolated from the cyanobacterium Anabaena cylindrica is reported. A first generation approach delivered one enantiomeric series of the polyketide fragment. Comparison of the 1H NMR data ...

2007

Synthesis of the C(1)-C(11) polyene fragment of apoptolidin with a new sulfur dioxide-based organic chemistry

Pierre Vogel, Laure Bouchez

A new sulfur dioxide-based organic chemistry has been developed as a novel approach for the stereoselective synthesis of polyene fragments based on our one-pot, four-component synthesis of polyfunctional alpha-alkanesulfonyl-gamma,delta-unsaturated ketones ...

2005

Particle size investigations of a multistep synthesis of PVA coated superparamagnetic nanoparticles

Heinrich Hofmann, Alke Fink, Mathieu Chastellain

Nanoscaled particles showing superparamagnetic behavior have been intensively studied in the past years for various applications. Nevertheless, the lack of well-defined particles remains an important problem. One of the major challenges is still the large- ...

2004