Article
Chemistry, Multidisciplinary
Yeruva Pavankumar Reddy, Shaik Anwar
Summary: An efficient protocol was developed for the construction of spiro pyrazolone tetrahydropyran scaffolds at ambient temperature without the use of any metal catalyst. The reaction involved the formal [4 + 2] cyclisation of trans-beta-nitro-styrene-derived Morita-Baylis-Hillman alcohol with alpha-arylidene pyrazolone. The synthesis followed an oxa-Michael/Michael cascade pathway and yielded new C-C and C-O bonds. The use of quinine-derived catalyst resulted in high enantiomeric excess (ee) and excellent diastereoselectivity (>20:1).
Article
Chemistry, Multidisciplinary
Cyprien Muller, Filip Horky, Marie Vayer, Andrei Golushko, David Leboeuf, Joseph Moran
Summary: This paper describes a new variant of the oxa-Pictet-Spengler reaction using epoxide as a starting material, which greatly expands the scope and rate of the reaction. By using hexafluoroisopropanol as a solvent, the electrophile scope of the reaction includes ketone analogues, aliphatic aldehydes, and phenylacetyl aldehydes, and the nucleophile scope includes moderately electronically deactivated and highly substituted beta-phenylethanols. In addition, the products can be further modified in the same system by subsequent ring-opening, reductions, and intra- and intermolecular Friedel-Crafts reactions. Finally, the synthesis of drug analogues demonstrates the pharmacological relevance of the isochroman motif.
Article
Chemistry, Multidisciplinary
Weijian Li, Meifen Jiang, Minjie Liu, Xu Ling, Yingqi Xia, Li Wan, Fener Chen
Summary: This study demonstrates the first fully continuous flow approach towards the asymmetric total synthesis of natural tetrahydroprotoberberine alkaloids. The method features a concise linear sequence without the need for intermediate purification, and involves four chemical transformations and three on-line work-up processing in an integrated flow platform.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Zhi Xu, Mikaela DiBello, Zechun Wang, John A. Rose, Lei Chen, Xin Li, Seth B. Herzon
Summary: In this study, a stereocontrolled synthesis of the fully glycosylated monomeric unit 3 of the cytotoxic bacterial metabolite (-)-lomaiviticin A was described. The synthesis involved a novel strategy and various coupling reactions, providing a foundation for completing the synthesis of (-)-lomaiviticin A itself.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Applied
Anastasia Kurbanova, Martin Nigrini, Kinga Golabek, Ondrej Vesely, Jan Vesely
Summary: Synthetic organic chemistry often requires multiple steps and expensive catalysts for the synthesis of functionalised tetrahydropyrans. In this study, we tested zeolites as eco-friendly and industrially relevant catalysts for the synthesis of 2-phenyltetrahydropyran. The results showed that zeolites favor the formation of the desired product, and the reaction kinetics depend on the number of acid sites, rather than the textural properties.
MICROPOROUS AND MESOPOROUS MATERIALS
(2023)
Review
Chemistry, Organic
Philip J. Chevis, Stephen G. Pyne
Summary: Asymmetric organocatalysis is a versatile method for enantioselective alpha-functionalization of aldehydes, with a focus on diverse catalysts and heteroatomic modifications. Research has also delved into understanding the catalytic cycle and reaction mechanisms, leading to the development of novel catalysts with superior chemoselectivity. Three general synthetic applications, including Horner-Wadsworth-Emmons, aldol, and organometallic addition reactions, are examined, along with examples of functional group chemistry and their downstream reactivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Polymer Science
Yu Song, Takehiko Gotoh, Satoshi Nakai
Summary: By using a cationic polymer gel-supported oxidising agent, arsenic can be efficiently removed from water with high adsorption capacity and removal rate, making it suitable for arsenic removal from industrial wastewater.
Review
Chemistry, Multidisciplinary
Guang-Jian Mei, Wai Lean Koay, Chuan Xiang Alvin Tan, Yixin Lu
Summary: Pyrroloindolines are important polycyclic indoline motifs widely found in natural products and bio-significant molecules, presenting a challenge to organic chemists with their rigid tricyclic molecular architectures and fully substituted carbon center at the C3a-position. Alkaloids containing pyrroloindoline display promising activities, making them significant in biological sciences and drug development. In recent decades, the synthetic targets of pyrroloindoline and analogues have attracted tremendous attention from the synthetic community, with a focus on catalytic asymmetric synthesis and total synthesis applications.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Multidisciplinary Sciences
Guang Li, Qian Wang, Jieping Zhu
Summary: While elegant asymmetric synthesis of Hasubanan alkaloids has been achieved in the past decades, a divergent approach to access all three subclasses of natural products remained unknown until now. The authors demonstrate enantioselective total syntheses of four representative members via a unified strategy, leading to three topologically different classes of alkaloids.
NATURE COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Gillian McArthur, Steven Abel, Giulio Volpin, David M. Barber
Summary: This review summarizes the methods and importance of enantioselective synthesis of 2-isoxazolines and 2-isoxazolin-5-ones with fully substituted stereocenters, as well as discusses the limitations and future developments in this research field.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Michael S. Crocker, Zihang Deng, Jeffrey N. Johnston
Summary: Amide synthesis is widely used in drug development and peptide synthesis, but waste elimination in this process has had limited success. Umpolung amide synthesis has been developed as a method for enantioselective synthesis, but it cannot forge N-aryl amides. This study presents a direct synthesis method for N-aryl amides using a simple Bronsted base as a promoter, using alpha-fluoronitroalkanes and N-aryl hydroxyl amines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Alex J. Vendola, Christophe Allais, Anne-Marie R. Dechert-Schmitt, James T. Lee, Robert A. Singer, James P. Morken
Summary: The Pt-catalyzed diboration of cyclic alkenes has been extended to unsaturated heterocycles and bicyclic compounds, achieving diastereoselective results. The study investigates optimal procedures, substrate scope, and diastereoselectivity, with examples of both homogeneous and heterogeneous catalysis. Application to the construction of the nucleoside analog (+/-)-aristeromycin was also demonstrated.
Article
Chemistry, Physical
Benjamen P. Reed, Sofia Marchesini, Giovanni Chemello, David J. Morgan, Neil Vyas, Thomas Howe, Jorg Radnik, Charles A. Clifford, Andrew J. Pollard
Summary: X-ray photoelectron spectroscopy (XPS) is commonly used for characterizing the chemistry of graphene-related two-dimensional materials (GR2M). However, the sample preparation method has a significant impact on the quantification results in XPS analysis. An investigation by three laboratories reveals that the preparation of oxygen-functionalized graphene nanoplatelet (GNP) powders affects the measured elemental composition in XPS. Pressing GNP powders onto adhesive tapes, into recesses, or into solid pellets leads to inconsistencies in the XPS quantification. The study recommends pelletizing powder samples of GR2Ms before XPS analysis to improve the repeatability and reproducibility of measurements.
Article
Chemistry, Multidisciplinary
Noah J. Sims, Weston C. Bonnet, Danielle M. Lawson, John L. Wood
Summary: Herein, the first total synthesis of (+)-alterbrassicicene C (2) is reported. Key features of this synthesis include an oxiranium mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and the installation of a vinyl methoxy ether moiety via Stille coupling.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Noah J. Sims, Weston C. Bonnet, Danielle M. Lawson, John L. Wood
Summary: This article describes the first total synthesis of (+)-alterbrassicicene C (2). Key features of the synthesis include an oxiranium-mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and installation of a vinyl methoxy ether moiety via Stille coupling.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)