A5017004547- Catalytic C–H Functionalization Methods
- Alkaloids: synthesis and pharmacology
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Oxidative Organic Chemistry Reactions
- Asymmetric Synthesis and Catalysis
- Traditional and Medicinal Uses of Annonaceae
- Synthetic Organic Chemistry Methods
- Chemical synthesis and alkaloids
- Radical Photochemical Reactions
- Synthesis of Indole Derivatives
- Chemical Synthesis and Analysis
- Catalytic Cross-Coupling Reactions
- Advanced Synthetic Organic Chemistry
- Microbial Natural Products and Biosynthesis
- Synthesis and Catalytic Reactions
- Synthesis and Biological Activity
- Sulfur-Based Synthesis Techniques
- Crystallography and molecular interactions
- Marine Sponges and Natural Products
- TiO2 Photocatalysis and Solar Cells
- Advanced Photocatalysis Techniques
- Cyclopropane Reaction Mechanisms
- Catalytic Processes in Materials Science
- Chemical Synthesis and Reactions
Centre National de la Recherche Scientifique
2016-2025
Institut de Chimie Moléculaire et des Matériaux d'Orsay
2016-2025
Université Paris-Saclay
2016-2025
Centre Hospitalier d'Orsay
2017-2020
Université Paris-Sud
2010-2019
University of Zurich
2017
Université de Lorraine
2016
Institut Parisien de Chimie Moléculaire
2011-2016
Université de Caen Normandie
2015
Centre Hospitalier Universitaire de Caen
2015
We report the use of electrochemistry to perform a direct oxidative dearomatization indoles leading 2,3-dialkoxy or 2,3-diazido indolines under undivided conditions at constant current. This operationally simple electro-oxidative procedure avoids an external oxidant and displays excellent functional group compatibility. The formation two C-O C-N bonds is believed arise from oxidation into radical cation intermediates.
Abstract Inspired by the biogenetic synthesis of benzofuroindoline‐containing natural products, we designed an oxidative coupling between phenol and N ‐acetyl indoles. This straightforward direct radical process, mediated 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone FeCl 3 allowed regioselective benzofuro[3,2‐b]indolines, whose structure is found in product phalarine.
IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3) features a rare example the reactivity indole core in Friedel-Crafts reaction. This umpolung allows us straightforward access to tetracyclic benzofuroindoline motif found natural product diazonamide A, which is potent antitumor agent.
In control! N-alkoxybicyclolactams derived from the ring-rearrangement metathesis of nitroso Diels–Alder cycloadducts were subjected to successive addition two nucleophiles yield substituted piperidine or pyrrolidine precursors with good excellent stereoselectivity. The relative configuration newly formed stereocenter can be controlled by order nucleophiles. Detailed facts importance specialist readers are published as "Supporting Information". Such documents peer-reviewed, but not...
The straightforward entry to benzofuroindoline containing natural product-like scaffolds has been achieved by a challenging [3 + 2] oxidative coupling between phenols and indoles. reaction proceeds NIS-oxidation of the indole followed trapping resulting electrophilic intermediate phenol.
The dearomative introduction of trifluoromethyl and 1,1-difluoroethyl radicals, generated from their corresponding sulfinate salts, into the C2 position indole derivatives allows diastereoselective synthesis three-dimensional 3,3-spirocyclic indolines over C–H functionalized indoles.
This Account summarizes our involvement in the development of dearomatization reactions indoles that has for origin a total synthesis problematic. We present effort from group to obtain 3D-indolines scaffold umpolung N-acyl via activation with FeCl3 oxidative spirocyclizations N-EWG and use electrochemistry. 1 Introduction 2 Activation N-Acyl Indoles 2.1 Hydroarylation 2.2 Difunctionalization 3 Radical-Mediated Dearomatization Synthesis Spirocyclic Indolines 4 Electrochemical 4.1 Direct...
We report an efficient and environmentally friendly electrochemical approach to perform the bromo cyclization of tryptophol, tryptamine tryptophan derivatives. The 3a-bromofuranoindolines 3a-bromopyrroloindolines obtained are interest in total synthesis natural products. This dearomative procedure relies on generation electrophilic bromine reagent by oxidation MgBr2. No organic byproducts generated with this protocol which avoids use additional electrolyte.
An efficient domino reaction combining different classes of pericyclic reactions leads to chiral complex polycyclic indoline-based architectures from achiral starting materials under mild conditions. This practical method is based on the ability iron(III) chloride promote both 4π electrocyclizations 2,4-dienals and C2–C3 umpolung N-acetylindoles during dearomative (3 + 2) cycloadditions.
We report the cyclization of 3-substituted N-acetylindoles for straightforward synthesis 3,3-spiroindolines via Friedel-Crafts reaction an appended aryl group or formal [2 + 2] cycloaddition alkene. Our strategy involves Umpolung C2═C3 bond indole nucleus during FeCl3-mediated hydroarylation annulation reactions.
The diastereoselective synthesis of α-amino phosphonate derivatives embedded in spirocyclic indolines is reported. present method proceeds via the dearomative addition phosphonyl radicals at C2-position indole nucleus oxidative conditions followed by intramolecular trapping resulting carbocation before rearomatization. trans-3,3-Spirocyclic 2-phosphonoindolines were thus obtained.
We report the challenging direct carbamoylation or cyanation of benzylic C(sp3)–H bonds with an isocyanide via electrochemical process giving rise to structures that are encountered in several biologically relevant compounds and drugs. This transformation proceeds under mild conditions without need for any external oxidant avoids necessity start from a prefunctionalized substrate deployment cation pool method. The anodic oxidation position subsequent addition lead formation C–C bond...
Out of the blue: The convergent asymmetric total synthesis antitumor antibiotic (−)-cribrostatin 4 from blue sponge Cribrochalina features Staudinger and Pictet–Spengler reactions to form tetrahydroisoquinoline moiety. These were followed by a reductive opening/elimination tricyclic β-lactam cyclization access unsaturated pentacyclic core.
Abstract A general methodology for the stereoselective synthesis of 2‐(2‐hydroxyalkyl)piperidine alkaloids by ring‐rearrangement metathesis nitroso Diels–Alder cycloadducts is reported. The approach illustrated formal porantheridine and total andrachcinidine through a diastereodivergent allylation an N ‐alkoxy bicyclic lactam. asymmetric latter alkaloid provides new insights into configurational stability between chloronitroso reagents cyclopentadiene.
A method for the direct and rare umpolung of 3 position indoles is reported. The activation N-acetylindole with iron(III) chloride allows C-H addition aromatic heteroaromatic substrates to C2=C3 double bond indole nucleus generate a quaternary center at C3 leads regioselectively 3-arylindolines. Optimization, scope (50 examples), practicability (gram scale, air atmosphere, room temperature), mechanistic insights this process are presented. Synthetic transformations indoline products into...
We report the first total synthesis of (-)-17-nor-excelsinidine, a zwitterionic monoterpene indole alkaloid that displays an unusual N4-C16 connection. Inspired by postulated biosynthesis, we explored oxidative coupling approach from geissoschizine framework to forge key ammonium-acetate Two strategies allowed us achieve this goal, namely intramolecular nucleophilic substitution on 16-chlorolactam with N4 nitrogen atom or direct I2 -mediated enolate geissoschizine.
Abstract We report an unprecedented domino polycyclization from readily available 2,4‐dienals and cyclic α,β‐unsaturated imines that is initiated by iso‐Nazarov reaction. This Brønsted acid promoted reaction enables the concomitant formation of four bonds, three cycles, contiguous stereogenic centers to yield elaborated structures in a single operation. A range fused hexacyclic molecules obtained highly diastereoselective manner.