Review
Chemistry, Multidisciplinary
Xingyu Shen, Danny Q. Thach, Chi P. Ting, Thomas J. Maimone
Summary: Annulation reactions, from Robinson annulation to Diels-Alder cycloaddition, have driven the advancement of natural product synthesis in the past century. The ability to form cyclic molecules directly from simpler fragments has transformed various aspects of chemical sciences. By combining annulation with oxidative rearrangement, a wide range of natural products containing bicyclo[3.3.1]nonane cores have been successfully synthesized, demonstrating the broad applicability of this strategy.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Gabrielle Robert-Scott, Jacob St-Gelais, Denis Giguere
Summary: The research developed a new method for the synthesis of C-2-symmetrical 1,4-dioxane-carbohydrate hybrid compounds, and prepared C-2-symmetrical glycomimetics through synthetic derivatization, which is of great significance for further biological investigations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sonu Yadav, S. S. V. Ramasastry
Summary: A conceptually novel intramolecular allylic alkylation strategy was developed for the synthesis of carbazoles and dibenzothiophenes, where palladium catalyses the formation of pi-allylpalladium complexes and facilitates the benzannulation process.
CHEMICAL COMMUNICATIONS
(2021)
Article
Multidisciplinary Sciences
Wataru Matsuoka, Hideto Ito, David Sarlah, Kenichiro Itami
Summary: Nanographenes and polycyclic aromatic hydrocarbons are important compounds with numerous applications, yet challenging to access. The authors present a diversity-oriented, growth-from-template synthesis of nanographenes enabled by iterative annulative pi -extension reactions from small PAH starting materials.
NATURE COMMUNICATIONS
(2021)
Review
Chemistry, Physical
Joseph R. H. Manning, Carlos Brambila, Siddharth V. Patwardhan
Summary: Research on design of porous sol-gel silica materials with amine additives is a thriving area, aiming to control the synthesis process. While progress has been made, there is still a difficulty in replicating the complexity of naturally occurring biosilica materials.
MOLECULAR SYSTEMS DESIGN & ENGINEERING
(2021)
Article
Chemistry, Applied
Dirgha Raj Joshi, Ikyon Kim
Summary: The study successfully achieved multi-functionalization of the pyridine motif in indolizine through [5+1] annulative construction, introducing three different functional groups at the C5, C6, and C7 positions. The solvent (2-MeTHF) and the hydroxyl of 2-hydroxyacetophenones were found to play crucial roles in the successful cyclization event. Furthermore, the elaboration of the resulting scaffold and the potential expansion using other methyl ketones were also demonstrated.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yifan Deng, Chia-Ping H. Yang, Amos B. Smith
Summary: The enantioselective total syntheses of (+)-peniciketals A and B have been achieved, with key synthetic transformations including ARC and Negishi cross-coupling, among others.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
M. Carmen de la Fuente, Yuri Segade, Katherine Valderrama, Jaime Rodriguez, Carlos Jimenez
Summary: The siderophore piscibactin is a key virulence factor involved in iron uptake by pathogenic bacteria causing fish diseases. A convergent total synthesis of its Ga3+ complex was described using L-/D-cysteine as chiral agents and Meldrum's acid. A Staudinger reduction/Aza-Wittig process was a key step in the synthesis of the acid-sensitive beta-hydroxy-2,4-disubstituted thiazoline moiety.
Article
Chemistry, Organic
Xue Wang, Hui-Lin Mao, Yu-Heng Yang, Hong Jiang, Ling-Qi Chen, Shu-Jiang Tu, Wen-Juan Hao, Bo Jiang
Summary: A palladium-catalyzed asymmetric annulative allylic alkylation reaction was developed for the regio- and enantioselective synthesis of dihydropyrido[1,2-a]indoles with a chiral cyclic allyl stereocenter. This protocol offers mild conditions, a broad substrate scope, and high regio- and stereoselectivities, providing a catalytic asymmetric route for the synthesis of chiral pyridoindole scaffolds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Environmental Sciences
Alexandra C. C. Cordova, Lucie C. C. Ford, Alan Valdiviezo, Alina T. T. Roman-Hubers, Thomas J. J. McDonald, Weihsueh A. A. Chiu, Ivan Rusyn
Summary: Cell-based testing of multi-constituent substances and mixtures for their potential adverse health effects is challenging due to their complex composition and physical-chemical characteristics. This study aimed to evaluate different scaled-down dosing methods for high-throughput in vitro testing of a mixture of polycyclic aromatic hydrocarbons (PAH). Among the tested dosing methods, media accommodated fraction (MAF) was determined to be the most suitable method for cell-based studies of PAH-containing complex substances and mixtures.
Article
Chemistry, Organic
Ruyu Xie, Zhiqiang Zhao, Yongxing Zhao, Rui Li, Jinzhong Yao, Maozhong Miao
Summary: Via Cu(I)-catalyzed cycloisomerization, readily available allenyl ketones bearing a cyclopropyl moiety can form in situ furan-fused cyclobutenes, which are highly reactive and powerful species that can undergo annulative fragmentation with terminal ynones to produce a wide variety of functional furans in moderate to high yields. This ring-distortion protocol features an unprecedented strain-controlled cycloisomerization/Diels-Alder/retro-Diels-Alder (CDRD) sequence under mild conditions.
Article
Chemistry, Organic
Ankita Paul, Diksha Rai, Kabita Pradhan, Preeti Balhara, Amar Kumar Mishra, Suvarn S. Kulkarni
Summary: Here, we describe the total synthesis of a complex tetrasaccharide repeating unit from Vibrio cholerae O43, which consists of rare deoxy amino sugars and an uncommon amino acid. The synthesis involves the preparation of protected sugars and unnatural amino acids, stereoselective construction of multiple glycosidic linkages, amide coupling, and the incorporation of nitrogen atoms and carboxylic acid functionality. The synthesis represents a challenging task due to the complexity of these reactions.
Article
Chemistry, Organic
Hui-Lin Mao, Yu-Xin Wang, Xue Wang, Hai-Ying Wang, Wen-Juan Hao, Bo Jiang
Summary: This article reports a palladium-catalyzed asymmetric annulative dearomatization of phenols with butene dicarbonate, enabling twofold decarboxylative allylation to selectively produce a range of spirocyclohexadienones with yields of 29-95% and enantioselectivity of 74-99%. A catalytic dearomative formal [4 + 2] cyclization of 1,1'-biphenyl-2,4'-diols delivered spiro[chromane-4,1'-cyclohexane]-2',5'-dien-4'-ones with high enantioselectivity, while enantioenriched spiro[cyclohexane-1,4'-quinoline]-2,5-dien-4-ones were generated starting from 2'-amino-[1,1'-biphenyl]-4-ols as 1,4-dinucleophiles.
Article
Chemistry, Multidisciplinary
Yannick Linne, Elisa Bonandi, Christopher Tabet, Jan Geldsetzer, Markus Kalesse
Summary: The first total synthesis of chondrochloren A was achieved using a 1,2-metallate rearrangement addition as an alternative to the Nozaki-Hiyama-Kishi reaction. This approach not only overcomes the challenges of the polyketide segment but also provides a novel strategy for assembling polyketidal frameworks, utilizing a Z-selective cross coupling to form the Z-enamide.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jiaxiang Wang, Jiahui Gao, Tianyun Guo, Xing Huo, Wenhua Zhang, Jian Liu, Xiaolei Wang
Summary: In this study, bioinspired total syntheses of A201A, A201D, and A201E were achieved based on a previously reported biosynthetic pathway. The challenging 1,2-cis-furanoside, a core structure of the A201 family, was obtained through remote 2-quinolinecarbonyl-assisted glycosylation. The total synthesis of A201A and A201E was accomplished without interference from basic dimethyl adenosine, and the absolute configuration of A201E was confirmed. This modular synthesis strategy allows efficient preparation of A201 family antibiotics, facilitating the study of their structure-activity relationships and mode of action.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Agriculture, Multidisciplinary
Wei Wang, Shan Zhang, Jianhua Wang, Furan Wu, Tao Wang, Gong Xu
Summary: A series of potential novel fungicides were designed and synthesized, with two compounds showing significant antifungal activities against various fungi. These compounds could be promising candidates for the development of new fungicides in crop protection.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Agriculture, Multidisciplinary
Wei Wang, Jianhua Wang, Furan Wu, Huan Zhou, Dan Xu, Gong Xu
Summary: A series of novel pyrazol-5-yl-benzamide derivatives were designed, synthesized, and evaluated for their antifungal activities. Compound 5IIc showed excellent in vitro and in vivo fungicidal activities, demonstrating its potential as a promising fungicide candidate. Additionally, molecular docking simulation and enzymatic inhibition assay provided insights into the mechanism of action of compound 5IIc.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Chemistry, Organic
Danyang Zhang, Dan Xu, Xinyue Chen, Huan Zhou, Gong Xu
Summary: This study demonstrates the conversion of a specific intermediate into members of the walsucochin family, leading to the total synthesis of (+/-)-walsucochin A, (+/-)-walsucochinoids C-F, and their analogues for the first time.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Page N. Daniels, Hyunji Lee, Rebecca A. Splain, Chi P. Ting, Lingyang Zhu, Xiling Zhao, Bradley S. Moore, Wilfred A. van der Donk
Summary: This study identified a new biosynthetic pathway in which glycyl-tRNA is used to attach amino acids to a ribosomally synthesized peptide, generating amino acid-derived natural products. This pathway involves multiple hydroxylations and chemical modifications.
Article
Biochemistry & Molecular Biology
Wei Wang, Xiang-Jia Liu, Guo-Tai Lin, Ji-Peng Wu, Gong Xu, Dan Xu
Summary: In this study, a series of N-(1H-pyrazol-5-yl)nicotinamide derivatives were designed, synthesized, and evaluated for their antifungal activities. Compound B4 exhibited good fungicidal activity against S. sclerotiorum and V. mali, and showed potential for suppressing rape sclerotinia rot caused by S. sclerotiorum.
CHEMISTRY & BIODIVERSITY
(2022)
Article
Chemistry, Organic
Hong-Wei He, Yuan Chi, Cai-Yun Chen, Fei-Yu Wang, Jia-Xin Wang, Dan Xu, Huan Zhou, Gong Xu
Summary: The synthesis of (+/-)nicotlactone A, a potent antiviral lignan with three continuous chiral centers, is reported in 5 steps from methyl acrylate. The synthetic compounds were evaluated for their anti-tobacco mosaic virus (anti-TMV) activity, and one of the synthesized compounds showed similar activity to a commercial agent, suggesting its potential as a candidate for developing novel antiviral agents in crop protection.
SYNTHESIS-STUTTGART
(2022)
Article
Agriculture, Multidisciplinary
Wei Wang, Jianhua Wang, Jipeng Wu, Mengyun Jin, Junling Li, Shiyang Jin, Wangxiang Li, Dan Xu, Xili Liu, Gong Xu
Summary: In this study, novel derivatives were synthesized and evaluated for their antifungal activities against various fungal species. Compound 9Ip showed promising in vitro and in vivo antifungal activities, potentially acting through interaction with succinate dehydrogenase.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Agriculture, Multidisciplinary
Hong-Wei He, Fei-Yu Wang, Danyang Zhang, Cai-Yun Chen, Dan Xu, Huan Zhou, Xili Liu, Gong Xu
Summary: A series of novel derivatives were synthesized based on the structure of nicotlactone A, and they exhibited good antiviral and antifungal activities, demonstrating their potential applications as antiviral and crop protection agents.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Chemistry, Organic
Rongrong Xie, Huan Zhou, Hui Lu, Yawei Mu, Gong Xu, Mingxin Chang
Summary: An efficient enantioselective reductive amination and amidation cascade reaction has been developed using iridium or rhodium complexes as catalysts. The coupling of simple alkyl diamines and alpha-ketoesters, assisted by sets of additives, smoothly leads to chiral cyclic piperazinone products. The reaction proceeds through distinctive types of intermediates for disubstituted and monosubstituted alkyl diamine substrates, and achieves high enantioselectivity with different transition metals, iridium for the former and rhodium for the latter.
Article
Chemistry, Multidisciplinary
Wen-Bo Han, Yi-Jie Zhai, Rong Zhang, Xu-Shun Gong, Jia-Qian Li, Gong Xu, Xinxiang Lei, Liangcheng Du, Jin-Ming Gao
Summary: A new family of oligomeric 10-membered macrolides, Tricrilactones A-H (1-8), featuring five unique ring skeletons, were isolated from Trichocladium crispatum fungus. Their structures and absolute configurations were determined using spectroscopic analysis, quantum chemical calculations, and X-ray diffraction analysis. The absolute configuration of compound 1's highly flexible side chain was resolved through asymmetric synthesis. The biosynthetic pathway for these macrolides was proposed using intermediate-trapping and isotope labeling experiments.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Richard S. Ayikpoe, Lingyang Zhu, Jeff Y. Chen, Chi P. Ting, Wilfred A. van der Donk
Summary: The domain of unknown function 692 (DUF692) is a family of enzymes involved in the biosynthesis of RiPP natural products. This study identified a new member of the DUF692 family, ChrH, and demonstrated its catalyzation of a unique chemical transformation. The characterization of ChrH expands the repertoire of reactions catalyzed by DUF692 enzymes.
ACS CENTRAL SCIENCE
(2023)
Editorial Material
Chemistry, Multidisciplinary
Yiwei Zhang, Chi P. Ting
Summary: This study presents a synthetic method for the construction of dimeric diketopiperazine alkaloids containing an unsymmetrical C3-N1' linkage. By releasing electrophilic iodine, the researchers successfully dimerized a designed tryptophan-alternative building block, leading to the concise synthesis of (+)-asperazine.
Article
Agriculture, Multidisciplinary
Yuan Chi, Hong-Wei He, Cai-Yun Chen, Si-Ying Zhao, Huan Zhou, Dan Xu, Xili Liu, Gong Xu
Summary: In this study, a series of novel sesamolin derivatives A0-A31 and B0-B4 were synthesized by simplifying the structure of furofuran lignan phrymarolin II. Their antiviral and antibacterial activities were systematically evaluated. The results showed that compound A24 displayed remarkable inactivation activity against tobacco mosaic virus (TMV), while compound A25 possessed prominent antibacterial activities. This research provides a solid foundation for the utilization of furofuran lignans in crop protection.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Yantao Li, Han Yang, Yidan Ma, Yuan Cao, Dan Xu, Xili Liu, Gong Xu
Summary: In this study, a series of novel benzamide derivatives incorporating a thiocyanato group into the pyrazole ring were synthesized and evaluated for their fungicidal activities against various fungi and pathogens. Compound A36 showed the highest antifungal activity against Valsa mali, while compound B6 exhibited the best anti-oomycete activity against Phytophthora capsici. Compound A27 displayed broad-spectrum inhibitory activities against multiple fungi and pathogens.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Organic
Wang Wei, Wu Furan, Ma Yidan, Xu Dan, Xu Gong
Summary: A series of novel fungicide derivatives were designed and synthesized using an active fragment splicing strategy. Compound 14 exhibited excellent antifungal activity against several strains and molecular docking simulation suggested its potential mechanism of action.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
