Article
Chemistry, Multidisciplinary
Qiao Song, Yan Liu, Linlin Cai, Xinyu Cao, Shan Qian, Zhouyu Wang
Summary: This study presents a straightforward method for the synthesis of fused indolizidines and quinolizidines from amides, which is conducted under mild conditions, exhibits good tolerance towards functional groups, can be easily scaled up, and is applicable for the total synthesis of various bioactive substances.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Audrey Mauger, Maxime Jarret, Aurelien Tap, Remi Perrin, Regis Guillot, Cyrille Kouklovsky, Vincent Gandon, Guillaume Vincent
Summary: We synthesized highly strained pentacyclic caged framework of mavacuran alkaloids and successfully achieved the concise total synthesis of C-fluorocurine, C-profluorocurine, C-mavacurine, normavacurine, 16-epi-pleiocarpamine and taberdivarine H. A strategy involving late-stage Michael addition and intermolecular 1,4-addition reactions was designed. The first total syntheses of C-profluorocurine and C-fluorocurine were achieved through dihydroxylation of C-mavacurine and a pinacol rearrangement, respectively.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Qijian Ni, Fangfang Xu, Xiaoxiao Song
Summary: An organocatalytic Michael/aza-Michael cascade reaction was developed for the synthesis of functionalized quinolizine scaffolds with high yields, excellent diastereoselectivity, and E/Z selectivity. This methodology involves the [3 + 3] annulation of 2-pyridylacetates with nitroenynes through dearomative strategy under mild conditions. The versatility of late-stage derivatizations further demonstrates the synthetic utility of this approach.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yulong Zhao, Jiaxin Li, Ruize Ma, Feifei He, Hongliang Shi, Xiaoguang Duan, Huilin Li, Xingang Xie, Xuegong She
Summary: The total synthesis of the indole alkaloid (-)-an-dranginine has been achieved in 10 steps, involving key reactions including nucleophilic addition of acetylenyl anion, intramolecular N-alkylation reaction, and dienyne metathesis cascade reaction.
Article
Chemistry, Multidisciplinary
Rui Yang, Zeyu Zhou, Huanfeng Jiang, Toh-Seok Kam, Kai Chen, Zhiqiang Ma
Summary: The first asymmetric total synthesis of the monoterpenoid indole alkaloid arboduridine has been achieved. The synthesis involves several reactions to construct the complex structure and demonstrates a highly enantioselective synthetic strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Seiya Katahara, Yasukazu Sugiyama, Mina Yamane, Yukinori Komiya, Takaaki Sato, Noritaka Chida
Summary: A five-step total synthesis of (+/-)-aspidospermidine based on a lactam strategy is reported, featuring an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade for the generation of a tricyclic ketone intermediate from a simple lactam. This strategy allows for easily available lactams to be used as stable surrogates of multisubstituted amines and could be applicable to a unified total synthesis of complex Aspidosperma alkaloids.
Article
Chemistry, Organic
Karina Amudi, Burak Kuzu, Seda Kolak, Hasan Genc, Nurettin Menges
Summary: 1H-Pyrrole reacted with lactone-type 2,3-furandione derivatives in anhydrous diethyl ether at room temperature to synthesize a series of pyrrolizinone derivatives in a single step without a catalyst. Various substituents were introduced in the pyrrolizinone derivatives, such as phenyl, substituted phenyl, thienyl, trifluoromethyl, naphthyl, biphenylyl, ester, or oxalate. The reaction conditions also led to the formation of pyrrolizino[1,2-a]pyrrolizin-5-ones with a novel skeleton when an excess of pyrrole was used. The purified molecules were obtained with high yields, up to 91%, and a gram-scale reaction yielded 0.952 g (71%) of the corresponding product.
Article
Chemistry, Organic
Huanhuan Zou, Jiahang Yan, Xiaocheng Zhang, Xiaohui Wu, Jiyou Huo, Yuanzhen Xu, Weiqing Xie
Summary: In this study, the asymmetric synthesis of (+)-vellosimine was achieved in 13 steps (longest linear sequences, LLS). The synthesis featured a sequential nucleophilic addition/cyclization process and highlighted the reductive cyclization of a ketone with an attached alpha,beta-unsaturated ester for constructing the strained quinuclidine moiety.
Article
Chemistry, Organic
Giacomo Mari, Lucia De Crescentini, Gianfranco Favi, Fabio Mantellini, Stefania Santeusanio
Summary: A novel protocol for the efficient synthesis of 1H-imidazo[5,1-c][1,4]oxazines has been developed by combining aza-Michael addition of selected primary amines to 1,2-diaza-1,3-dienes (DDs) with isothiocyanates or isocyanates in a sequential 3-component reaction (3-CR) process, resulting in 2-thiohydantoins and hydantoins with suitably positioned functional groups for chemoselective acid-promoted ring-fused formation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chao Liu, Luc Van Meervelt, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A novel gold-catalyzed hydroarylation/Michael addition process has been developed for the efficient construction of benzazepinoindole polycyclic scaffolds from readily accessible multifunctional Ugi adducts. The developed methodology exhibits a broad substrate scope, excellent functional-group tolerance, and high yields of the target benzazepinoindoles.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Brian J. Knight, Ryan C. Harbit, Joel M. Smith
Summary: This article presents a concise approach to the synthesis of lysergic acid using simple aromatic precursors. The strategy involves coupling, dearomatization, and cyclization reactions, leading to the synthesis of a novel neuroactive compound, 12-chlorolysergic acid, in just 6 steps from commercially available starting materials. The use of dearomative retrosynthetic analysis offers important advantages in this design.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Weijian Li, Meifen Jiang, Wenchang Chen, Yu Chen, Zhi Yang, Pei Tang, Fener Chen
Summary: A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids was achieved in three steps, utilizing efficient strategies for synthesis and introducing the desired stereochemistry at the C-14 position. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as structurally related non-natural analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Santiago J. Bolivar J. Avila, Gabriela N. N. Ledesma, Teodoro S. S. Kaufman, Sebastian A. Testero, Enrique L. L. Larghi
Summary: An efficient and straightforward route to synthesize the isatin-type natural product melosatin A was reported. A trisubstituted aniline was used as a key intermediate, which was synthesized in 4 steps and yielded 60% overall. The final step involved the Martinet cyclocondensation of the key aniline with diethyl 2-ketomalonate, resulting in a 68% yield of the natural product.
Article
Chemistry, Multidisciplinary
Xiu-Ning Hu, Dong-Ping Wu, Ye-Peng Xu, Pei-Qiang Huang
Summary: The first organocatalytic asymmetric synthesis of an advanced intermediate of (+)-sarain A was achieved by combining organocatalytic asymmetric Michael addition reaction and a nitrogen-to-carbon chirality transfer. This method allows for the construction of three chiral centers and chemoselective reduction of a key lactam intermediate, providing a tricyclic intermediate with all necessary functionalities for further elaboration into (+)-sarain A.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Jun-Jie Wang, Rui-Xue Bai, Mao-Qi Yang, Zheng-Yu Chen, Min-Dan Wang, Qian Zhao, Guo-Qiang Lin, Jian-Guo Fu, Chen-Guo Feng
Summary: The total synthesis of (-)-amathaspiramide A was achieved through the efficient construction of a chiral aza-spirobicyclic core using the aldol addition/transamidification cascade. The scope of the efficient construction methodology was investigated, and configuration adjustment via an asymmetric protonation process was identified as a vital step to obtain the correct stereochemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
M. Spadina, S. Dourdain, J. Rey, K. Bohinc, S. Pellet-Rostaing, Jean-Francois Dufreche, T. Zemb
Summary: This article discusses the application of ienaic modeling for the solvent extraction of rare earths using a mixed DMDOHEMA/HDEHP extractant system. The study compares experimental findings with theoretical predictions of the droplet model, showing that different behaviors in the extraction process depend on the acidity and mole fraction of extractants.
SOLVENT EXTRACTION AND ION EXCHANGE
(2022)
Article
Chemistry, Multidisciplinary
S. Dourdain, M. Spadina, J. Rey, K. Bohinc, S. Pellet-Rostaing, Jean-Francois Dufreche, T. Zemb
Summary: Efficient formulations in hydrometallurgy often rely on the synergistic action of two oil-soluble extractants at an optimized mole fraction. This study investigates the DMDOHEMA/HDEHP system and how synergistic effects vary with acidity, presenting experimental results and proposing a theoretical model for interpreting the acid effect on synergism and antagonism.
SOLVENT EXTRACTION AND ION EXCHANGE
(2022)
Review
Astronomy & Astrophysics
Michele Fiore, Carolina Chieffo, Augustin Lopez, Dimitri Fayolle, Johal Ruiz, Laurent Soulere, Philippe Oger, Emiliano Altamura, Florence Popowycz, Rene Buchet
Summary: Phospholipids are crucial components of biological membranes and play roles in cell signaling, enzymatic reactions, and energy metabolism. They also have significant implications in the emergence of life. Recent advancements have provided a deeper understanding of these unique hydrophobic molecules and their essential functions in cell biology. There is now growing interest in prebiotic lipidomics, calling for a reevaluation of these important biomolecules.
Article
Polymer Science
Ruth Oye Auke, Guilhem Arrachart, Romain Tavernier, Ghislain David, Stephane Pellet-Rostaing
Summary: A solid-phase extraction system was investigated for the extraction and recovery of rare-earth elements. Phenolic ion-exchange resins were synthesized using a non-toxic aromatic dialdehyde as a substitute for toxic formaldehyde. The resins showed a high ion-exchange capacity and the ability to back-extract the rare-earth elements using an acid solution.
Article
Biochemistry & Molecular Biology
Thomas Chetot, Xavier Serfaty, Lena Carret, Alexandre Kriznik, Sophie-Rahueal-Clermont, Lucie Grand, Maiwenn Jacolot, Florence Popowycz, Etienne Benoit, Veronique Lambert, Virginie Lattard
Summary: Four coding splice variants of Pdi pre-mRNA were discovered in rats. The consensus sequence and the third splice variant were found to be fully active, while the second splice variant was less active than the consensus sequence.
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS
(2023)
Article
Chemistry, Organic
Grand Lucie, Powderly Marian, Popowycz Florence, Jacolot Maiwenn
Summary: The regio- and diastereoselective synthesis of chiral amines derived from 1,4-D-sorbitan has been achieved through the borrowing hydrogen reaction, using a cooperative catalysis between an achiral iridium catalyst and diphenylphosphoric acid. The differential reactivities of the four hydroxyl groups on the 1,4-D-sorbitan scaffold have also been emphasized.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Guillaume Mossand, Evan Lelong, Chen Xing, Frantz Ndebulia Watchou, Antoine Leydier, Guilhem Arrachart, Stephane Pellet-Rostaing
Summary: This work presents the synthesis of formo-phenolic resins containing CAM moieties combined with phenol, catechol or resorcinol. These chelating resins have been developed for selective extraction of U(VI) from seawater, which poses challenges due to its high pH and abundant alkaline and earth-alkaline cations. Results from sorption experiments show that the synthesized resins exhibit good sorbent properties for U(VI), with a maximum uptake capacity of about 50 mg/g and pronounced selectivity for uranium even in saline conditions. Thermodynamic and kinetic adsorption data were determined using Langmuir adsorption model and pseudo-second order model for the best resin.
Article
Chemistry, Organic
Jingjing Jiang, Yves Queneau, Florence Popowycz
Summary: The use of the renewable platform molecule 5-HMF in multi-component reaction with a diamine and an alkynone to generate seven-membered 1,5-benzodiazepines is described. Ammonium acetate in ethanol proved to be a clean and efficient system among catalysts/solvents couples. The optimized conditions were used to investigate the scope of the reaction providing a library of 1,5-benzodiazepines in moderate to good yields from a wide range of diversely substituted diamines and alkynones or alkyl alkynoates.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Malvina Larduinat, Jordan Franc, Maiwenn Jacolot, Florence Popowycz
Summary: In this study, the Ir(III)-catalyzed synthesis of 3-pyrrolidinols and 4-piperidinols by reacting 1,2,4-butanetriol or 1,3,5-pentanetriol with primary amines was demonstrated. This borrowing hydrogen methodology was also applied to the sequential diamination of triols, leading to the formation of amino-pyrrolidines and aminopiperidines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Sarah Asaad, Marwa Hamandi, Guilhem Arrachart, Stephane Pellet-Rostaing, Serge Kimbel, Stephane Daniele
Summary: Efficient and selective extraction of precious and critical metal ions was achieved using zirconia nanoparticles modified with organic carbamoyl phosphonic acid ligands. The modification of commercial ZrO2 dispersed in aqueous suspension was achieved through optimizing the Bronsted acid-base reaction in ethanol/H2O solution. The modified ZrO2 showed promising stability, efficiency, and reusability in industrial applications for selective gold recovery, with di-N,N-butyl carbamoyl pentyl phosphonic acid ligand showing the highest adsorption efficiency and hydrophobicity playing a significant role.
Editorial Material
Chemistry, Multidisciplinary
Guillaume Mossand, Evan Lelong, Chen Xing, Frantz Ndebulia Watchou, Antoine Leydier, Guilhem Arrachart, Stephane Pellet-Rostaing
Summary: This study reports the synthesis of formo-phenolic resins with catecholamide moieties for selective extraction of U(VI) from seawater. The synthesized materials showed good sorbent properties and a pronounced selectivity for uranium, even under saline conditions. Thermodynamic and kinetic adsorption data were determined for the best resin using the Langmuir adsorption model and pseudo-second order model.
Article
Biochemistry & Molecular Biology
Nolan Chatron, Manon Boulven, Adrien Montagut-Romans, Flavien Ponsot, Maiwenn Jacolot, Herve Caruel, Etienne Benoit, Florence Popowycz, Virginie Lattard
Summary: Vitamin K antagonists (VKAs) have been widely used as anticoagulants, but resistance to these drugs due to VKORC1 mutations has been a challenge. In this study, the crystal structure of VKORC1 provided new insights for the development of new anticoagulants. By combining chemical synthesis, enzymatic assays and molecular modelling, a structure-activity relationship model was established, showing that lipophilicity, membrane permeability and affinity towards human VKORC1 enzyme are key factors for potent anticoagulants.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Jordan Francois, Jordan Rio, Erwann Jeanneau, Marie-Eve L. Perrin, Maiwenn Jacolot, Pierre-Adrien Payard, Florence Popowycz
Summary: Taking advantage of our preliminary observations, we successfully achieved the direct C-C borrowing hydrogen functionalization on isosorbide using an Ir-based organometallic homogeneous catalyst with excellent diastereocontrol. The reaction involves a catalytic dehydrogenation, in situ aldol condensation/crotonisation, and a catalytic dehydrogenation to yield the desired homologated product. Through a computational mechanistic investigation, we elucidated the stereoelectronic effects and the roles of the Na counter-cation in guiding the hydride addition and coordinating the substrate's oxygen atoms, thus rationalizing the experimental selectivity at the molecular level.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Johal Ruiz, Josephine G. LoRicco, Laurent Soulere, Marta Salvador Castell, Axelle Grelard, Brice Kauffmann, Erick J. Dufourc, Bruno Deme, Florence Popowycz, Judith Peters
Summary: Archaeal membrane lipids have unique structures that enable them to withstand extreme temperature and pressure conditions. A study on the synthesis of an archaeal lipid called 1,2-di-O-phytanyl-sn-glycero-3-phosphoinositol (DoPhPI) derived from myo-inositol reveals its resistance mechanisms. The experiments show that DoPhPI and DoPhPC can form small vesicles in aqueous dispersions, and these dispersions undergo phase transitions from lamellar to cubic and hexagonal phases with increasing temperature. The phytanyl chains in the lipid also contribute to the bilayer's dynamic properties over a wide temperature range. These findings suggest that the unique properties of archaeal lipids provide plasticity and aid in resisting extreme conditions.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Physical
Simon Stemplinger, Jeremy Causse, Sylvain Prevost, Stephane Pellet-Rostaing, Thomas Zemb, Dominik Horinek
Summary: This study investigates a derivative of the classic surfactant Aerosol OT with a shorter chain length. The short chain derivative exhibits high solubility and progressively weak aggregation. The hydration of head groups hinders the penetration into hydrophobic cores, resulting in well-defined liquid chain nanodomains. The unusual small angle X-ray scattering pattern is attributed to the sulfonate group of the head groups rather than the aggregate-aggregate interaction.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
