Article
Chemistry, Multidisciplinary
Goh Sennari, Kristen E. Gardner, Stefan Wiesler, Maximilian Haider, Alina Eggert, Richmond Sarpong
Summary: Guided by chemical network analysis, the synthetic studies towards C18- and C19-benzenoid cephalotane-type norditerpenoids were carried out, leading to the construction of core structure in a concise manner and improvement of efficiency through reaction optimization.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Prashant Kumar, Pravesh Kumar, Sugumar Venkataramani, S. S. V. Ramasastry
Summary: This study reveals a new chemical reactivity pattern of allylic gem-diacetates and successfully synthesizes complex benzo[f]chromene compounds, demonstrating the versatility of the method. Additionally, interesting photochromic properties of the new classes of benzo[f]chromenes are discovered.
Article
Chemistry, Physical
Prashant Kumar, Pravesh Kumar, Sugumar Venkataramani, S. S. V. Ramasastry
Summary: This work explores the unusual chemical reactivity pattern of allylic gem-diacetates and establishes them as new prototypes for synthesizing complex benzo[f]chromene systems. The versatility of the method in synthesizing bioactive natural products based on chromene is demonstrated, along with the discovery of interesting photochromic properties of the new classes of benzo[f]chromenes.
Article
Chemistry, Applied
Mirdyul Das, Arantxa Rodriguez, Pui Kin Tony Lo, Wesley J. Moran
Summary: This study presents the preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates, allowing for a versatile range of substrates to be converted into substituted oxazolidinones ready for further transformations. Derivatization of the products at both ends is demonstrated in addition to a preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Jia-Hao Xie, Chao Zheng, Shu-Li You
Summary: A novel Pd-catalyzed method for dearomative methoxyallylation of 3-nitroindoles with allyl carbonates has been developed, achieving high yields and diastereoselectivity. The method demonstrates good scalability and practicality with relatively low catalyst loading. Kinetic experiments suggest that the nucleophilic attack of the alkoxide anion is the rate-determining step in this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Sebastian Wienhold, Lukas Fritz, Tatjana Judt, Sabrina Hackl, Thomas Neubauer, Bastian Sauerer, Thorsten Bach
Summary: A convergent strategy was developed for the synthesis of the C12-C40 segment of (-)-pulvomycin, involving a diastereoselective aldol reaction between a chiral ethyl ketone and a chiral aldehyde. The desired anti-aldol product was obtained in a total yield of 5% over 16 steps, containing 12 out of 13 stereogenic centers present in the natural product.
SYNTHESIS-STUTTGART
(2021)
Review
Chemistry, Multidisciplinary
Xiaohong Huo, Guanlin Li, Xi Wang, Wanbin Zhang
Summary: Bimetallic catalysis is an efficient strategy for developing new chemical reactions and stereodivergent synthesis, allowing for the preparation of products with different stereoisomers from the same set of starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Plant Sciences
Srijit Das, Hussein Sakr, Isehaq Al-Huseini, Raghu Jetti, Sara Al-Qasmi, Raju Sugavasi, Srinivasa Rao Sirasanagandla
Summary: There are various herbicides used in agriculture, including the water-soluble herbicide Atrazine (ATZ) which has been found to have toxic effects on different systems of the body. ATZ can enter the body through various routes and has been associated with deleterious effects on respiratory, reproductive, endocrine, central nervous, gastrointestinal, and urinary systems. Some studies have even shown a link between ATZ exposure and cancer in industrial workers. This review discusses the mechanism of ATZ toxicity and explores the potential use of natural products as alternative treatments.
Article
Chemistry, Multidisciplinary
Pu-Sheng Wang, Liu-Zhu Gong
Summary: Pd-catalyzed asymmetric allylic C-H functionalization is a powerful tool to access chiral and densely functionalized molecules from easily accessible alkenes, resulting in increased step- or atom-economy by minimizing functional group manipulations. However, due to inadequate stereoselection strategies, this field is still in its early stage. This essay describes the journey to identify asymmetric catalytic systems, the mechanism of allylic C-H activation, control of stereo- and regioselectivity, and applications in asymmetric synthesis.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaochen Tian, Yongxing Zhang, Hao Dong, Weiwu Ren, Yang Wang
Summary: The asymmetric alpha-regioselective annulation of MBH carbonates with 4-arylmethylisoxazol-S-ones has been developed, resulting in the synthesis of spirocyclic oxindole derivatives with three contiguous stereogenic centers and vicinal all-carbon quaternary chiral centers. This reaction exhibits a broad substrate scope and excellent functional group tolerance, producing high yields with high diastereo- and enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Pharmacology & Pharmacy
Qinfang Zheng, Ye Wang, Shuihan Zhang
Summary: This work reviews the progress in the phytochemical and biological investigations of bioactive components from Lobelia species, highlighting the shift in research focus towards novel chemical classes and molecular mechanisms of these components.
FRONTIERS IN PHARMACOLOGY
(2021)
Article
Nutrition & Dietetics
Maria Sorokina, Kira S. McCaffrey, Erin E. Deaton, Guoying Ma, Jose M. Ordovas, Penelope M. Perkins-Veazie, Christoph Steinbeck, Amnon Levi, Laurence D. Parnell
Summary: This manuscript introduces a catalog of 1,679 small molecules occurring in watermelon and their cheminformatics analysis for diverse features, highlighting the importance of this catalog for precision nutrition and plant breeding efforts. Improved and comprehensive collections of natural products accessible to the public will be especially useful for researchers in nutrition, cheminformatics, bioinformatics, and drug development.
FRONTIERS IN NUTRITION
(2021)
Article
Chemistry, Multidisciplinary
Yinsong Zhao, Shaozhong Ge
Summary: The structural diversity of sp(3)-triorganometallic reagents enhances their potential in modular construction of molecular complexity in chemical synthesis. We report a selective triborylation reaction of unactivated alkenes to access synthetically versatile 1,1,3-triborylalkanes. This reaction provides a general platform for regioselective trifunctionalization of unactivated alkenes, and its utility is highlighted by the synthesis of various value-added chemicals from readily accessible unactivated alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Andreis M. Durantini, Lloyd Lapoot, Shakeela Jabeen, Goutam Ghosh, Johirul Bipu, Serah Essang, Britney C. Singh, Alexander Greer
Summary: Although silica surfaces have been used in organic oxidations for the production of peroxides, the study of airborne singlet oxygen at interfaces is limited and has not found widespread advantages. In this study, prenyl phenol-coated silica and delivery of singlet oxygen through the gas phase were used to achieve significant selectivity for dihydrofuran formation over allylic hydroperoxide formation. The mechanism of selectivity was further investigated using air/nanoparticle interfaces and density functional theory calculations.
Review
Engineering, Chemical
Prima F. Hillman, Chaeyoung Lee, Sang-Jip Nam
Summary: Wound healing is challenging in clinical settings and requires proper management. Acute wound healing involves cell divisions, formation of extracellular matrix, and the release of growth factors and cytokines. Factors like infection and inflammation can delay healing, and natural products have shown potential in promoting wound healing. This review discusses the research on wound healing activities of natural microbial products, aiming to contribute to the development of better wound treatments.
Article
Chemistry, Multidisciplinary
Bernhard Wolfl, Nils Winter, Jiajing Li, Adam Noble, Varinder K. Aggarwal
Summary: The development of preparative methods for the synthesis of four-membered carbocycles is important for their utility in medicinal chemistry. A new methodology for producing spirocyclic epoxides and aziridines with a cyclobutane motif was developed. The reaction is efficient and can tolerate a broad variety of substrates. The products can be used as modular building blocks for introducing three-dimensional structures into target molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Sheenagh G. Aiken, Joseph M. Bateman, Hsuan-Hung Liao, Alexander Fawcett, Teerawut Bootwicha, Paolo Vincetti, Eddie L. Myers, Adam Noble, Varinder K. Aggarwal
Summary: In this study, a highly efficient iterative strategy for the synthesis of polyacetates based on boronic ester homologation was reported. It does not require functional group manipulation between iterations. This methodology has been applied to the synthesis of bahamaolide A and has demonstrated versatility in various stereospecific transformations.
Article
Chemistry, Organic
Joseph C. Abell, Christian P. Bold, Laia Vicens, Tom Jentsch, Noelia Velasco Perez, Jasper L. Tyler, Robert N. Straker, Adam Noble, Varinder K. Aggarwal
Summary: Aza-spirocycles, highly rigid and three-dimensional structures, have been incorporated into pharmaceuticals due to their beneficial pharmacokinetic properties. We report a simple synthesis of spirocyclic dihydropyridines through an electrophile-induced dearomatization reaction, which offers the potential for rapid assembly of medicinally relevant spirocycles.
Letter
Hematology
Justin S. Trory, Attila Munkacsi, Kamila M. Sledz, Jordan Vautrinot, Lucy J. Goudswaard, Molly L. Jackson, Kate J. Heesom, Samantha F. Moore, Alastair W. Poole, Behnam Nabet, Varinder K. Aggarwal, Ingeborg Hers
Article
Chemistry, Multidisciplinary
Qi Lin, Hao Lan, Chunmiao Ma, Ryan T. Stendall, Kenneth Shankland, Rebecca A. Musgrave, Peter N. Horton, Carsten Baldauf, Hans-Joerg Hofmann, Craig P. Butts, Manuel M. Mueller, Alexander J. A. Cobb
Summary: We present the first structures of an unusual helix formed by a heteromeric sequence of alpha- and delta-amino acids and demonstrate its application in catalysis. The helix formation is driven by intramolecular hydrogen bonds, but we also observed an apolar interaction that stabilizes one type of helix over another. This unique stabilization enables the alpha-residues to engage in bifunctional catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lydia I. Dewis, Madhavachary Rudrakshula, Christopher Williams, Elisabetta Chiarparin, Eddie L. Myers, Craig P. Butts, Varinder K. Aggarwal
Summary: Using α-helix mimetics as inhibitors of protein-protein interactions is a prevalent therapeutic strategy. Controlling the conformation of mimetics through destabilizing syn-pentane interactions can enhance their efficacy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Patrick Moon, Charlotte M. Zammit, Qian Shao, Dustin Dovala, Lydia Boike, Nathaniel J. Henning, Mark Knapp, Jessica N. Spradlin, Carl C. Ward, Helene Wolleb, Daniel Fuller, Gabrielle Blake, Jason P. Murphy, Feng Wang, Yipin Lu, Stephanie A. Moquin, Laura Tandeske, Matthew J. Hesse, Jeffrey M. McKenna, John A. Tallarico, Markus Schirle, F. Dean Toste, Daniel K. Nomura
Summary: While vaccines and antivirals are available to combat the SARS-CoV-2 pandemic, additional antiviral therapeutics are needed for future coronaviruses. The coronavirus Main Protease (Mpro) is a promising target for antiviral therapies. This study discovered and optimized cysteine-reactive pyrazoline-based covalent inhibitors for SARS-CoV-2 Mpro, which showed nanomolar potency against not only SARS-CoV-2, but also other coronaviruses. These findings provide potential chemical scaffolds for future pancoronavirus inhibitors.
Review
Chemistry, Multidisciplinary
Jasper L. Tyler, Varinder K. Aggarwal
Summary: The use of metalated (aza)bicyclo[1.1.0]butanes in synthesis is experiencing a revival, with numerous reports in the past 5 years demonstrating their ability to undergo unique transformations or generate novel fragments. These species have been found to participate in a wide range of reactions, facilitating rapid diversification of (aza)bicyclo[1.1.0]butane-containing compounds. The investigation into their reactivity has led to the elucidation of reaction mechanisms involving strained bicycles and will solidify their importance in organometallic chemistry.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Ze-Shu Wang, Steven H. H. Bennett, Bilal Kicin, Changcheng Jing, Johan A. A. Pradeilles, Karen Thai, James R. R. Smith, P. David Bacos, Valerio Fasano, Carla M. M. Saunders, Varinder K. K. Aggarwal
Summary: In this study, a novel strategy for the construction of dihydrobenzofurans and indolines was described. The aromatic ring was created through an inverse-electron demand Diels-Alder reaction and a cheletropic extrusion sequence, followed by an aromatization process. The methodology was successfully applied in the total synthesis of the antiplatelet drug beraprost and the synthesis of functionalized indolines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Maryam Bashir, Muhammad Arshad, Robina Begum, Varinder K. Aggarwal
Summary: A highly selective asymmetric synthesis of a potent anti-TB drug (-)-bedaquiline was achieved through sulfur ylide asymmetric epoxidation, using (+)-isothiocineole as a chiral sulfide. The construction of the key diaryl epoxide exhibited excellent enantioselectivity (er 96:4) and diastereoselectivity (dr 90:10), followed by a highly regioselective ring opening (96:4). The synthesis was completed in nine steps starting from commercially available aldehyde with an overall yield of 8%.
Article
Chemistry, Multidisciplinary
Ethan S. Toriki, James W. Papatzimas, Kaila Nishikawa, Dustin Dovala, Andreas O. Frank, Matthew J. Hesse, Daniela Dankova, Jae-Geun Song, Megan Bruce-Smythe, Heidi Struble, Francisco J. Garcia, Scott M. Brittain, Andrew C. Kile, Lynn M. McGregor, Jeffrey M. McKenna, John A. Tallarico, Markus Schirle, Daniel K. Nomura
Summary: Targeted protein degradation with molecular glue degraders has emerged as a potent therapeutic approach for eliminating disease-causing proteins that are traditionally difficult to target. This study identifies a design strategy for converting protein-targeting ligands into covalent molecular glue degraders. By appending a covalent handle to a CDK4/6 inhibitor, the authors induce the degradation of CDK4 and demonstrate the effectiveness of this strategy for targeting various disease-associated proteins. This research provides valuable insights for the development of novel therapeutic interventions.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Jingjing Wu, Chao Shu, Zhihang Li, Adam Noble, Varinder K. Aggarwal
Summary: This article describes a visible-light photoredox-catalyzed decarboxylative halogenation reaction using inexpensive inorganic halide salts as halogenating agents. Bromination with lithium bromide can be achieved using an organic photoredox catalyst under simple conditions, while chlorination requires dual photoredox-copper catalysis. The reaction exhibits excellent functional group tolerance and can convert structurally complex natural products into alkyl bromides and chlorides. Additionally, the method is also applicable to thiocyanation reactions with potassium thiocyanide for the synthesis of alkyl thiocyanates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Kristian J. Chambers, Patthadon Sanghong, Daniel Carter Martos, Giorgia Casoni, Rory C. Mykura, Durga Prasad Hari, Adam Noble, Varinder K. Aggarwal
Summary: Enones are important functional groups in chemical synthesis and molecular biology. This study developed a one-pot strategy for the stereospecific conversion of boronic esters into enones using methoxyallene as a three-carbon building block. The methodology is versatile and has been successfully applied to the total synthesis of polyketide 10-deoxymethynolide.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Correction
Chemistry, Organic
Sebastien Prevost, Karen Thai, Nina Schutzenmeister, Graeme Coulthard, William Erb, Varinder K. Aggarwal
