A5061991312- Synthetic Organic Chemistry Methods
- Oxidative Organic Chemistry Reactions
- Marine Sponges and Natural Products
- Traditional and Medicinal Uses of Annonaceae
- Parkinson's Disease Mechanisms and Treatments
- Chemical Synthesis and Analysis
- Asymmetric Synthesis and Catalysis
- Marine Toxins and Detection Methods
- Carbohydrate Chemistry and Synthesis
- Microbial Natural Products and Biosynthesis
- Synthesis and Catalytic Reactions
- Click Chemistry and Applications
- Alzheimer's disease research and treatments
- Chemical synthesis and alkaloids
- Cholinesterase and Neurodegenerative Diseases
- Synthesis and Biological Evaluation
- Adenosine and Purinergic Signaling
- Chemical Synthesis and Reactions
- Botulinum Toxin and Related Neurological Disorders
- Porphyrin and Phthalocyanine Chemistry
- Radical Photochemical Reactions
- Plant-derived Lignans Synthesis and Bioactivity
- Polyoxometalates: Synthesis and Applications
- Axial and Atropisomeric Chirality Synthesis
- Catalytic C–H Functionalization Methods
Centre National de la Recherche Scientifique
2016-2025
Université Paris-Saclay
2016-2025
Laboratoire des Biomolécules
2021-2024
Université Paris-Sud
2010-2020
Institut Galien Paris-Saclay
2012-2015
Laboratoire d'Excellence en Recherche sur le Médicament et l'Innovation Thérapeutique
2012-2014
University of Pittsburgh
2013
Laboratoire de Chimie Organique
2005-2009
Université de Rouen Normandie
2009
ParisTech
2008-2009
The endoperoxide scaffold is found in numerous natural products and synthetic substances of pharmaceutical interest. main challenge to their access remains the preparation chiral compounds due weakness peroxide bond, which limits scope available or applicable methods. Here, we demonstrate how peroxycarbenium species can be trapped by silylated nucleophiles with high enantioselectivities diastereoselectivities when applicable, using a imidophosphorimidate (IDPi) as catalyst. methodology...
Several studies have reported that the tetracycline (TC) class antibiotic doxycycline (DOX) is effective against Parkinson's disease (PD) pathomechanisms. The aim of present work was three-fold: (i) Establish a model system to better characterize neuroprotection by DOX; (ii) Compare rescue effect DOX other TC antibiotics; (iii) Discover novel neuroprotective TCs having reduced activity. For that, we used cultures mouse midbrain dopamine (DA) neurons and experimental conditions iron-mediated...
Oncogenic metabolism depends on multifaceted mechanisms, including bidirectional inter-organelle communication between mitochondria and the nucleus, facilitating cellular adaptation at transcriptomic, proteomic, metabolomic levels. The mitochondrial protein complex composed of apoptosis-inducing factor (AIF) coiled-coil-helix-coiled-coil-helix domain-containing 4 (CHCHD4) is essential for this mitochondrio-nuclear communication. AIF/CHCHD4 mediates import cysteine-enriched nuclear...
A chemoselective synthesis of the macrocyclic core leucascandrolide has been achieved, utilizing highly enantioselective allylmetalations, an Noyori reduction a propargylic ketone and olefin metatheses as key steps.
A chemoselective synthesis of 1, the macrocyclic core leucascandrolide A, has been achieved by utilizing highly enantioselective allylmetalations, an Noyori reduction a propargylic ketone, and olefin metatheses as key steps.
[structure: see text] A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield 13%.
Parkinson's disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss midbrain dopamine neurons and disruption dopamine-mediated neurotransmission. There currently no curative treatment for this disorder. To discover druggable neuroprotective compounds neurons, we have designed synthesized second-generation quinoxaline-derived molecules based on structure–activity relationship studies, which led previously to discovery our first brain...
Abstract Herein we report the use of catalytic amount scandium(III) triflate or indium(III) chloride (with trimethylsilyl chloride) for functionalization endoperoxyacetals through Sakurai Mukaiyama reactions. These catalysts allow milder and more practical conditions than those previously reported with improvements in scope reproducibility. This method allows a full sequence from cyclopropanols to produce desired functionalized 1,2‐dioxolanes. magnified image
The synthesis of acetoxyendoperoxyacetal derivatives allowed the formation functionalized 3,5-disubstituted 1,2-dioxolanes through reactive peroxycarbenium species under Lewis acid mediation. introduction a neutral nucleophile such as allylsilane, silane, or silyl enol ether was accomplished with moderate to good yields. two studied acids, TiCl4 and SnCl4, gave contrasting results. higher diastereoselectivity toward trans diastereomer in experiments explained by faster degradation cis isomer...
Cyclobutanols undergo an oxidative ring expansion with Co(acac)2 and triplet oxygen to give 1,2-dioxanols. The formation of alkoxy radical drives the regioselective cleavage on more substituted side before insertion molecular oxygen. reaction is particularly effective secondary cyclobutanols but works also certain tertiary alcohols. Further substitution neutral nucleophiles under catalytic Lewis acid conditions led original 1,2-dioxanes a preferred 3,6-cis-configuration.
Amphidinolides F, C, C2, and C3 are marine natural products isolated from dinoflagellates Amphidinium species. They share the same macrolactone core, with difference between them residing at side chain level. A predominant feature of these amphidinolides is presence two trans-THF rings inside which thought to be built by C-glycosylation titanium enolate N-acetyl oxazolinethiones. Thus, original strategy for their total synthesis was based on assembly three main fragments corresponding C1–C9,...
Plakortides make up a subclass of marine endoperoxides with diverse biological activities. Their structural particularity is derived from the C
The synthesis of the C(1)−C(9) fragment amphidinolides C, C2, and F was achieved by using a vinyloguous Mukaiyama aldol reaction on chiral aldehyde with silyloxyfuran C-glycosylation lactol derivative an acetyl oxazolidinethione. From available acetonide−glyceraldehyde, all stereogenic centers were perfectly induced along synthesis. synthesized as vinyl stannane at C(9) in 10 steps, 16% yield.
A new and efficient convergent approach toward the synthesis of amphidinolide F is described through assembly three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate bulky N-acetyloxazolidinethiones. side chain was inserted Liebeskind–Srogl cross-coupling reaction. sulfone condensation/desulfonylation sequence, Stille cross-coupling, macrolactonization applied to connect
A tetrahydroisoquinoline identified in Mucuna pruriens ((1R,3S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline-1,3-dicarboxylic acid, compound 4) was synthesized and assessed for its vitro pharmacological profile vivo effects two animal models of Parkinson's disease. Compound 4 inhibits catechol-O-methyltransferase (COMT) with no affinity the dopaminergic receptors or dopamine transporter. It restores dopamine-mediated motor behavior when it is co-administered L-DOPA to C. elegans...
A diverse set of functionalized alpha,beta-unsaturated carbonyl compounds were synthesized in good yield by utilizing a very simple one-pot process involving cross-metathesis between acryloyl chloride and terminal olefin followed the addition nucleophile.
Intramolecular cycloadditions of bicyclo[1.1.0]butylalkyl-amines represent a rich source novel heterocyclic scaffolds. As function the side chain attached to amine, formal ene- or [2 + 2] cycloaddition products can be obtained in moderate high yields. By suitable further functionalizations, library 3-azatricyclo[5.1.1.0 1,5 ]-nonanes was prepared and interrogated 450 biological assays. This discovery collection found generate hit rates yet individual samples demonstrated sufficient...
[reaction: see text]. A short synthesis of lactone lignans exploiting a three-component coupling strategy is presented using new Lewis acid catalyzed ring-opening/cyclization reaction 2-methoxytetrahydrofuran derivatives 4 leading to gamma-butyrolactones as key step. By simply changing the conditions, it was possible, from same substrates 4, obtain selectively cyclopropane derivatives.