Article
Chemistry, Multidisciplinary
Miao Bai, Shihu Jia, Jingyang Zhang, Hong-Gang Cheng, Hengjiang Cong, Shanshan Liu, Zhiqian Huang, Yaoguo Huang, Xiaoming Chen, Qianghui Zhou
Summary: This article presents a modular and convergent method for the rapid assembly of 1,3-trans-disubstituted THIQ frameworks, highlighting the broad synthetic utility of this approach in the synthesis of naphthylisoquinoline alkaloids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Plant Sciences
Xiaojie Li, Jifa Zhang, Qifeng Chen, Pan Tang, Ting Zhang, Qiyi Feng, Jiajun Chen, Yun Liu, Feng-Peng Wang, Cheng Peng, Yong Qin, Liang Ouyang, Kai Xiao, Xiao-Yu Liu
Summary: A series of new derivatives were synthesized from the diterpenoid alkaloids deltaline and talatisamine through a diversity-oriented synthesis strategy. These derivatives demonstrated strong anti-inflammatory effects and were able to suppress the secretion of inflammatory factors. The representative derivative deltanaline showed potent anti-inflammatory activity in both in vitro and in vivo models, making it a promising lead compound for the treatment of inflammatory diseases.
Article
Chemistry, Multidisciplinary
Huajian Zhu, Yunrui Cai, Shijia Ma, Yushi Futamura, Jinbiao Li, Wen Zhong, Xiangnan Zhang, Hiroyuki Osada, Hongbin Zou
Summary: Utilizing secologanin as a starting material, a diversity-oriented synthesis approach was developed to successfully synthesize novel pseudo-natural alkaloids, laying the foundation for producing polycyclic products with multiple chiral centers. These newly constructed molecules showed antimalarial and highly potent neuroprotective properties after preliminary activity screening.
Article
Chemistry, Applied
Tsai-Hui Lung, Yi-Ru Chen, Chen-Ling Chang, Wey-Chyng Jeng, Pei-Shan Wu, Sandip Sambhaji Vagh, Gangababu Marri, Yi-Fang Lin, Wenwei Lin
Summary: A catalyst-controlled diversity-oriented synthesis of spirohydroquinoline-indandiones and 3-methylenehydroquinoline-indandiones was reported using ortho-sulfonamidophenyl-substituted para-quinone methides and allylidene-indandiones. Organobases such as DMAP or TMG were utilized to selectively control the reaction pathway, resulting in products with yields of 40-99% and excellent diastereoselectivities. Mechanistic studies revealed that spirohydroquinoline-indandione was the kinetic product, which underwent an unusual base-initiated 1,3-nitrogen rearrangement process to afford 3-methylenehydroquinoline-indandione in the presence of TMG.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Lu Chen, Guang Li, Liansuo Zu
Summary: Total synthesis of natural products is crucial due to their structural complexity and biological activities. The rapid construction of core skeletons, precise stereochemistry control, and suitable synthons identification are key concerns, where rearrangement reactions can simplify the overall synthesis process.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Organic
Dhruba Jyoti Boruah, Lodsna Borkotoky, Uma Devi Newar, Ram Awatar Maurya, Panneerselvam Yuvaraj
Summary: Multicomponent reactions (MCRs) are powerful tools in synthetic chemistry for efficiently synthesizing diverse molecular scaffolds, particularly nitrogen-containing heterocycles. However, the use of transition metal catalysts or additives in MCRs can have limitations due to cost, toxicity, and environmental concerns. This review focuses on recent advancements in transition metal-free MCRs for synthesizing valuable N-heterocyclic compounds and highlights their potential as sustainable and efficient strategies for accessing nitrogen-containing heterocycles.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Miranda J. Baran, Mark E. Carrington, Swagat Sahu, Artem Baskin, Junhua Song, Michael A. Baird, Kee Sung Han, Karl T. Mueller, Simon J. Teat, Stephen M. Meckler, Chengyin Fu, David Prendergast, Brett A. Helms
Summary: A diversity-oriented synthetic strategy has been developed to identify microporous polymer membranes that feature solvation cages for lithium ions, showing higher ionic conductivity and cation transference number. These membranes have potential applications as anode-stabilizing interlayers in high-voltage lithium metal batteries.
Article
Chemistry, Multidisciplinary
Hua-Wei Liu, Peng He, Wen-Tao Li, Wei Sun, Kai Shi, You-Qin Wang, Qian-Kun Mo, Xin-Yu Zhang, Shou-Fei Zhu
Summary: The application of computational tools in catalyst design has been limited due to the neglect of mechanistic data. In this study, we propose a new catalyst design strategy, catalyst-oriented design based on elementary reactions (CODER), which combines computational tools with researcher experience and fully utilizes mechanistic data. By using CODER, highly efficient Pd catalysts for C-N coupling were developed, significantly improving the synthesis efficiency of widely used triarylamine optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Polymer Science
In-Hwan Lee, Ki-Taek Bang, Hee-Seong Yang, Tae-Lim Choi
Summary: Diversification of polymer structures is crucial for unique applications, and diversity-oriented polymerization (DOP) using multicomponent polymerization (MCP) has emerged as an efficient strategy. Cu-catalyzed MCP (Cu-MCP) has overcome previous challenges in MCP, paving the way for diverse and complex polymer structures. Future research will focus on the advancement and optimization of Cu-MCP for innovative polymer applications.
MACROMOLECULAR RAPID COMMUNICATIONS
(2022)
Review
Chemistry, Organic
Ranjay Shaw, Amr Elagamy, Ismail Althagafi, Akhilesh Kumar Srivastava, Ramendra Pratap
Summary: Heterocycles are important scaffolds with building block properties and biological activities. Various synthesis methods have been used, with a focus on environmentally friendly approaches. There is a wealth of literature on sustainable and multi-component synthetic methods, but it can be challenging for researchers to keep up, making a review article necessary.
CURRENT ORGANIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Alexey Yu. Sukhorukov
Summary: This review summarizes the Nef and Meyer reactions as key transformations of aliphatic nitro compounds, with a focus on the interrupted versions in which the normal pathway is redirected by an external nucleophile. These processes greatly enhance the synthetic potential of nitro compounds. The prospects of this methodology in diversity-oriented organic synthesis are analyzed. The bibliography includes 90 references.
Article
Chemistry, Organic
Saikumar Banda, Alexander Villinger, Malte Brasholz
Summary: The dihydroazepino[1,2-a]indole diones 3 can be easily synthesized by catalytic photooxygenation of cyclohepta[b]indoles 1 followed by dehydration. A Lewis acid-catalyzed oxa Diels-Alder reaction of enones 3 with enol ethers 4 has been developed, leading to the formation of novel tetracyclic azepane-fused pyrano[3,2-b]indoles 5 with high stereoselectivity under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tristan Schuh, Olga Kataeva, Hans-Joachim Knoelker
Summary: We report the synthesis and X-ray crystal structure of mu-oxo-bis[(octacosafluoro-meso-tetraphenylporphyrinato)iron(iii)] [(FeTPPF28)(2)O]. This novel iron complex acts as an efficient catalyst for oxidative biaryl coupling reactions of diarylamines and carbazoles. The asymmetric oxidative coupling, in the presence of an axially chiral biaryl phosphoric acid as co-catalyst, provides 2,2'-bis(arylamino)-1,1'-biaryls with 96% ee. Additionally, the Wacker-type oxidation of alkenes to ketones with (FeTPPF28)(2)O as catalyst and phenylsilane as reductant proceeds at room temperature with air as the terminal oxidant, resulting in increased ketone/alcohol product ratios for internal and aliphatic alkenes.
Review
Chemistry, Multidisciplinary
Jian-Xing Xu, Le-Cheng Wang, Xiao-Feng Wu
Summary: Carbonylative multi-component reactions (CMCR) are an efficient strategy for the preparation of polyfunctional carbonylated compounds, using four or more starting materials. Diverse CMCR utilizing non-noble transition-metal catalysts have been developed. This review summarized and discussed the recent advances in non-noble metal-catalyzed carbonylative multi-component reactions.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Review
Chemistry, Medicinal
Bi-Shuang Chen, Di Zhang, Fayene Zeferino Ribeiro de Souza, Lan Liu
Summary: This review discusses the research progress on marine-derived alkaloid synthesis via enzymatic reactions, as well as the advantages and disadvantages of their applications for industrial production and the green chemistry for marine natural product research.
Article
Chemistry, Multidisciplinary
Adam I. Green, Fruzsina Hobor, Christopher P. Tinworth, Stuart Warriner, Andrew J. Wilson, Adam Nelson
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Medicinal
George Karageorgis, Samuel Liver, Adam Nelson
Article
Chemistry, Multidisciplinary
Adam I. Green, Christopher P. Tinworth, Stuart Warriner, Adam Nelson, Natalie Fey
Summary: Dirhodium(II) catalysts have diverse properties, and a database based on DFT-calculated parameters has been developed to aid in catalyst selection and exploration of reactivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Jacob R. Hauser, Edmund T. Bergstrom, Alexander N. Kulak, Stuart L. Warriner, Jane Thomas-Oates, Robin S. Bon
Summary: A series of pyrene-based LDI reagents (LALDI tags) have been developed for labeling and analyzing reducing carbohydrates in complex biological samples without the need for additional chemical derivatization or purification. The study demonstrates the potential of LALDI-MS for glycomics and diagnostics by direct detection of lactose in cow's milk.
Article
Chemistry, Multidisciplinary
Anthony Aimon, Mark J. Dow, Abigail R. Hanby, Ephraim A. Okolo, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: The stereocontrolled synthesis of complex spirotricyclic systems containing an embedded syn-1,2-diaminocyclohexane unit is achieved through a dearomatising oxidation of phenols bearing pendant ureas capable of acting as double nucleophiles. The resultant products possess rich functionality suitable for the synthesis of potentially bioactive compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ephraim A. Okolo, Axel Pahl, Sonja Sievers, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: A 'top down' scaffold remodelling approach was used to synthesize a library of spirotricyclic ureas via complexity-generating oxidative dearomatisation. Eighteen structurally distinct, sp(3)-rich scaffolds were obtained from the parent tricycle through ring addition, cleavage, and expansion strategies. Biological screening of the compound library based on these scaffolds revealed diverse phenotypic responses, highlighting both functional and structural diversity of the compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Rafal Kulmaczewski, Isaac T. Armstrong, Pip Catchpole, Emily S. J. Ratcliffe, Hari Babu Vasili, Stuart L. Warriner, Oscar Cespedes, Malcolm A. Halcrow
Summary: Four bis[2-{pyrazol-1-yl}-6-{pyrazol-3-yl}pyridine] ligands were synthesized and their complexes with iron (II) were studied. The results show that the torsion of the linker group can influence the conformation and spin state of the complexes.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Alexandra Hindle, Krzysztof Baj, Jonathan A. Iggo, Daniel J. Cox, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: A convergent approach to diazabicyclic scaffolds containing twisted amides or anilines is achieved through photocatalysed hydroamination and subsequent cyclisation of cyclic enecarbamates. The modular synthesis enables variation of the degree of twist and consequently the properties of the amides and anilines.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Daniel Francis, Sannia Farooque, Archie Meager, Didi Derks, Abbie Leggott, Stuart Warriner, Alex J. O'Neill, Adam Nelson
Summary: Activity-directed synthesis (ADS) is a function-driven method for discovering bioactive small molecules. In this study, algorithms were developed to design arrays of photoredox-catalysed alkylation reactions based on similarity to known bioactive reactions. The approach successfully expanded a series of antibacterial quinazolinones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Kristina Hetherington, Som Dutt, Amaurys A. Ibarra, Emma E. Cawood, Fruzsina Hobor, Derek N. Woolfson, Thomas A. Edwards, Adam Nelson, Richard B. Sessions, Andrew J. Wilson
Summary: The study introduces a computationally validated workflow for modifying the sequence of peptide inhibitors of protein-protein interactions.
RSC CHEMICAL BIOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Samuel D. Griggs, Alejandro Martin-Roncero, Adam Nelson, Stephen P. Marsden
Summary: This study reports a regioselective gamma-C-H amination method for the side-chain of saturated 2-alkyl nitrogen heterocycles, which proceeds through a sulfamide-directed 1,6-radical translocation. The practicality of this rapid access to 1,3-diamines is highlighted in a short synthesis of the alkaloid tetraponerine T8 and non-natural analogues.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Scott Rice, Daniel J. Cox, Stephen P. Marsden, Adam Nelson
Summary: Regioselective and stereospecific directed C-H arylation of simple amine substrates, followed by cyclisation, resulted in the synthesis of 30 diverse, three-dimensional scaffolds. This unified approach significantly expanded the range of bridged ring systems containing both a nitrogen atom and an aromatic ring.
CHEMICAL COMMUNICATIONS
(2021)
Review
Biochemistry & Molecular Biology
Adam Nelson, George Karageorgis
Summary: This minireview discusses methods that draw inspiration from natural products to focus on biologically-relevant areas of chemical space, potentially leading to more systematic discovery of unexplored regions in biologically-relevant chemical space.
RSC MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Alexandre F. Trindade, Emily L. Faulkner, Andrew G. Leach, Adam Nelson, Stephen P. Marsden
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Abbie Leggott, Justin E. Clarke, Shiao Chow, Stuart L. Warriner, Alex J. O'Neill, Adam Nelson
CHEMICAL COMMUNICATIONS
(2020)