A5101431230- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Synthetic Organic Chemistry Methods
- Cyclopropane Reaction Mechanisms
- Catalytic Alkyne Reactions
- Asymmetric Synthesis and Catalysis
- Catalytic C–H Functionalization Methods
- Marine Sponges and Natural Products
- Oxidative Organic Chemistry Reactions
- Organoboron and organosilicon chemistry
- Chemical Synthesis and Reactions
- Traditional and Medicinal Uses of Annonaceae
- Cancer Treatment and Pharmacology
- Microbial Natural Products and Biosynthesis
- Synthesis and Biological Evaluation
- Synthesis and Catalytic Reactions
- Sulfur-Based Synthesis Techniques
- Quantum Dots Synthesis And Properties
- Axial and Atropisomeric Chirality Synthesis
- Advanced Synthetic Organic Chemistry
- Cyclization and Aryne Chemistry
- Molecular Junctions and Nanostructures
- Adenosine and Purinergic Signaling
- Molecular spectroscopy and chirality
- Chemical Synthesis and Analysis
Centre National de la Recherche Scientifique
2003-2025
Centrale Marseille
2017-2025
Aix-Marseille Université
2009-2024
Institut des Sciences Moléculaires de Marseille
2011-2016
Université de Tours
2009
Institut de Chimie Moléculaire de Paris : organique, inorganique et biologique
2006-2008
Institut Parisien de Chimie Moléculaire
2007-2008
University of Cambridge
2007-2008
Laboratoire de Chimie Organique
2002-2008
Institut de Chimie
2007-2008
Abstract magnified image A general and efficient copper(I)‐catalyzed cross‐coupling heterocyclization reaction of terminal alkynes β‐iodo‐α,β‐unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields a variety 5‐ylidenebutenolides 3‐substituted isocoumarins with regio‐ stereoselectivity. procedure does not require the use any expensive supplementary additives, is palladium‐free.
A concise route to the ABC and ABCD core of molecules isolated from genus Schisandra has been accomplished. The synthesis demonstrated high atom efficiency employing a new one-pot cascade which sequentially built three rings quaternary spirocenter.
We describe an operationally simple, good-yielding, two-step cascade process to convert biscyclopropanes 1 into high-value benzocyclobutene building blocks 3. This study highlights the novel reactivity of our "in-house" donor-acceptor cyclopropane, achieving complete diastereoselectivity and regioselectivity transfer.
Abstract Enediynes undergo intramolecular [2+2+2] cycloaddition in the presence of cobalt(II) iodide (CoI 2 ), manganese and an N‐heterocyclic carbene (IPr) generated situ from corresponding imidazolium salt butyllithium (BuLi). Polycyclic cyclohexadienes are obtained selectively. This new method represents interesting alternative to those employing air‐sensitive cyclopentadienylcobalt [CpCoL (L=CO, C H 4 )] catalysts. Moreover, can be used catalytically, which is a significant improvement...
A single-crystal-to-single-crystal solid-state reaction of vinylogous donor–acceptor cyclopropanes is documented. The enantiospecific synthesis new products, distinct from those obtained in solution, achieved for the target compounds. Photopolymerization occurred upon X-ray exposure to crystals. Notably, one case, this reactivity exhibits selectivity since an ordered arrangement polymers and unreacted cocrystallized monomeric conformers has been observed. Structural characterization complete...
[reaction: see text] The first examples of totally chemo- and regioselective formal intermolecular cobalt(I)-catalyzed [2 + 2 2] cyclizations three different alkynes are reported. use disposable silylated tethers in the sequence cyclization followed by displacement silicon group led to polysubstituted arenes as a unique cycloadduct high yields.
Actin class: A stereoselective synthesis of the microfilament-destabilizing cytotoxic macrolide (−)-reidispongiolide A, isolated from marine sponge Reidispongia coerulea, uses a convergent aldol-based strategy to construct 26-membered macrolactone, followed by coupling with an N-vinylformamide subunit. This constitutes first any member reidispongiolide/sphinxolide family. Supporting information for this article is available on WWW under...
Abstract A stereocontrolled total synthesis of the microfilament‐destabilizing cytotoxic macrolide (−)‐reidispongiolide A, isolated from New Caledonian marine sponge Reidispongia coerulea , is described. This utilizes a convergent aldol‐based strategy to construct 26‐membered macrolactone, followed by late‐stage coupling derived aldehyde with an N ‐vinylformamide‐containing ketone subunit install full side chain. Two alternative routes were examined for introduction 2 E ,4 ‐dienoate region,...
Stereogenic main group elements, a promising strategy for metal-free enantioselective catalysis.
[reaction: see text] A new and efficient sequence of two consecutive cyclizations, a cobalt(I)-mediated [2 + 2 2] cyclotrimerization Diels-Alder reaction, is proposed to allow the formation ABC core taxoids in 65% overall yield, starting from an acyclic polyunsaturated precursor.
Abstract The synthetic utility of γ‐alkylidenebutenolides is demonstrated as highly competent dipolarophile partners in both intra‐ and intermolecular rhodium(II)‐catalyzed 1,3‐dipolar cycloaddition reactions. strength this approach lies the formation spiro[6,4]lactone moieties with concomitant construction quaternary spiro stereocenters. Typically, spirolactones involves an esterification step, which has often been reported a “biosynthetic pathway”, occurs either or near to final step total...
[reaction: see text] A new and efficient procedure for the preparation of unsymmetrical silaketals via a three-step protocol without isolation intermediates is presented. The silyl ethers silanes can also be readily obtained this sequence reactions.
Abstract A combination of a cobalt( I )‐mediated cyclotrimerization and [4+2] reaction is described as new entry into the ABC core taxanes. The [4+2]/[2+2+2] [2+2+2]/[4+2] pathways both lead to expected title compound. Mechanistic proposals are understand formation side products during [2+2+2] cycloaddition apply useful modifications highly substituted unsaturated precursors. Indeed, we demonstrate, for first approach, that substitution at propargylic position has dramatic influence on...
Abstract An access to functionalised eight‐membered carbocyclic ring compounds was developed by simply stirring an unusual vinylogous Donor‐Acceptor Cyclopropane (DAC) in boiling o ‐xylene. Both experimental and computational studies were performed explain the diastereoselectivity/regioselectivity transfer observed provide overall picture of mechanism. magnified image
The synthesis of new C-6 1,2,3-triazole adenosine derivatives via microwave assisted 1,3-dipolar cycloaddition as key step is described. binding on membranes cells that over express A(1) receptors (A(1)AR) was also evaluated. Among them, four compounds increased cAMP production, in a dose-dependent manner acting antagonists the A(1)AR, while two act agonists.
We recently discovered that a linear multifunctional trimethylsilylacetylene (TMSA) compound forms long-range and highly stable self-assembled monolayers (SAMs) on reconstructed Au(111). To better understand the interactions governing self-assembly in this new system, we synthesized series of homologue organosilanes performed scanning tunneling microscopy (STM) measurements at Au(111)/n-tetradecane interface. The four TMSA-terminated silanes self-assemble similar ways gold, with molecules...
A new reactivity of donor–acceptor cyclopropanes (DACs) has been highlighted and, for the first time, we report that they could formally behave as nucleophiles and be functionalized at their C3 position. The cyclopropane acts a formal nucleophilic synthetic equivalent 1,2‐zwitterion described an umpolung synthon. highly substituted lactone is reached, even more impressive formation four stereogenic centers with complete control relative configuration. Both experimental computational studies...
The expeditious construction of a highly functionalized ABC core ingenol via an intramolecular, metal-free [6+4] cycloaddition cycloheptatrienone and furan is reported.
The BCD tricyclic core of brownin F was prepared in eight synthetic operations for the first time. Our synthesis features a diastereo-, chemo- and regioselective intramolecular [3 + 2] cycloaddition between cyclic carbonyl ylide γ-alkylidenebutenolide.