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Concept

Alcaloïde indolique

Publications associées (25)

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

Catalytic enantioselective Pictet-Spengler reaction of carbonyl compounds: Development and application to the asymmetric total synthesis of indole alkaloids

Rémi Julien Sylvain Andres

This thesis consists in an extensive study about the enantioselective Pictet-Spengler reaction (EPSR) and its application to the total synthesis of monoterpene indole alkaloids (MIAs). The general introduction presents the literature background about this ...

EPFL2022

Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine

Qian Wang, Jieping Zhu, Alexandre Julien Florent Leclair

A single-electron transfer (SET) oxidation of indole or benzo[b]thiophene to a radical cation reverses the intrinsic polarity of these pi-excessive bicyclic heteroarenes. Here we report an oxidative two-carbon homologation of cyclobutanols to cyclohexenone ...

AMER CHEMICAL SOC2022

Enantioselective Total Synthesis of (+)-Nordasycarpidone, (+)-Dasycarpidone, and (+)-Uleine

Qian Wang, Jieping Zhu, Bastien Delayre, Cédric Fung

The structure of uleine type alkaloids is characterized by the presence of a bridged tetracyclic hexahydro-1H-1,5-methanoazocino[4,3-b]indole ring system 1. Various strategies have been developed to access this polycyclic structural motif. We report herein ...

2021

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

Palladium-Catalyzed Enantioselective Cacchi Reaction: Asymmetric Synthesis of Axially Chiral 2,3-Disubstituted Indoles

Qian Wang, Jieping Zhu, Hua Wu

We report herein the first examples of a palladiumcatalyzed enantioselective Cacchi reaction for the synthesis of indoles bearing a chiral C2-aryl axis. In the presence of a catalytic amount of Pd(OAc)2 and (R,R)-QuinoxP* ligand, reaction of N-aryl(alkyl)s ...

Wiley-VCH Verlag GmbH2020

Development of Photocatalysts towards the Visible-Light driven C-Terminal Bioconjugation of Peptides and Proteins

Marion Marie-Agnès Garreau

If small molecules have led to tremendous progress in curing diseases, new therapeutic agents such as peptides or antibody-drugs conjugates have emerged as a highly promising next generation of pharmaceuticals. As for small molecules, their derivatization ...

EPFL2020

Stereoselective Total Synthesis of Eburnane-Type Alkaloids Enabled by Conformation-Directed Cyclization and Rearrangement

Qian Wang, Jieping Zhu, Cyril Piemontesi, Guang Li

Controlling the cis C20/C21 relative stereochemistry remains an unsolved issue in the synthesis of eburnane-type indole alkaloids. Provided herein is a simple solution to this problem by developing a unified and diastereoselective synthesis of four represe ...

Wiley-VCH Verlag GmbH2019

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

"Divergent Total Synthesis of (-)-Rhazinilam, (-)-Leucomidine B and (+)-Leuconodine F" and "Synthetic Studies Towards Sarpagine-Related Indoles"

Dylan Jean Robert Dagoneau

The work presented in this thesis focuses on the synthesis of monoterpene indole alkaloids. The first part describes the divergent total synthesis of (-)-rhazinilam, (-)-leucomidine B and (+)-leuconodine F, three structurally distinct natural products of t ...

EPFL2017

Catalytic Asymmetric Tandem Reaction of Tertiary Enamides: Expeditious Synthesis of Pyrrolo[2,1-a]isoquinoline Alkaloid Derivatives

Jieping Zhu

Reported is a new and efficient strategy for rapid construction of the chiral tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one structure from unique tertiary enamide synthons. A Cu(OTf)2/chiral Pybox complex catalyzes the intramolecular enantioselective addit ...

Wiley-Blackwell2016

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

2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed C(sp(3))-H Functionalization of Trifluoroacetimidoyl Chlorides

Nicolai Cramer, Julia Pedroni

Perfluoroalkylated indoles are valuable compounds in drug discovery. A Pd(0)-catalyzed C(sp(3))-H functionalization enables access to 2-(trifluoromethyl)indoles from trifluoroacetimidoyl chlorides. These are stable compounds, easily obtained from anilines. ...

American Chemical Society2016

A New Perspective in the Use of FeOx-TiO2 Photocatalytic Films: Indole Degradation in the Absence of Fe-Leaching

César Pulgarin, Juan Kiwi, Sami Rtimi

The study addresses the degradation of Indole under low intensity solar simulated light. The first evidence is presented for sputtered films degrading Indole at the solid-air interface. The co-sputtering of FeOx-TiO2 on polyethylene (PE) leads to an accele ...

Elsevier2016

Platinum-Catalyzed Domino Reactionwith Benziodoxole Reagents for Accessing Benzene-Alkynylated Indoles

Jérôme Waser, Yifan Li

Indoles are omnipresent in natural products, bioactive molecules, and organic materials. Consequently, their synthesis or functionalization are important fields of research in organic chemistry. Most works focus on installation or modification of the pyrro ...

Wiley-Blackwell2015

Catalytic Friedel-Crafts Reaction of Aminocyclopropanes

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil

A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups ...

American Chemical Society2013

Indole Alkaloids Synthesis via a Selective Cyclization of Aminocyclopropanes

Jérôme Waser, Filippo De Simone

The continuous progress in medicinal chemistry requires more versatile synthetic strategies for the generation of large libraries of active compounds and their analogues. As a result, the research for new effective cyclization and cycloaddition reactions i ...

2012

Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis

Jérôme Waser, Filippo De Simone

The regioselective and diastereoselective cyclization of acyliminium intermediates generated from aminocyclopropanes on unprotected indoles is presented. The recent results obtained in our group are compared with previous intermolecular reactions with amin ...

2011

Concise Synthesis of Pyrrolidine and Indolizidine Alkaloids by a Highly Convergent Three-Component Reaction

Philippe Renaud, Kurt Schenk

The synthesis of pyrrolidine and indolizidine derivatives through radical carboazidation of alkenes with alpha-iodoketones, followed by reductive amination, is described. When properly substituted, further lactamization afforded pyrrolizidinones in good yi ...

2011

Biologically active secondary metabolites from cyanobacteria

Cyril Portmann

For millennia, nature was the only source of medicine for mankind. Even today natural products represent a large proportion of the drugs in use. In some areas, like cancer or infectious diseases, about 50 % of the compounds used are of natural origin. Cyan ...

EPFL2010