Reducing the prevalence of phytopathogens and their impact on crops is essential to reach sustainable agriculture goals. Synthetic pesticides have been commonly used to control crop disease but are now strongly linked to disease resistance, environmental pollution, depletion of soil biodiversity, and bioaccumulation, leading to adverse effects on human health. As a alternative, the prolific Trichoderma genus has been studied for its biocontrol properties, as well as its ability to promote plant growth and increase nutrient uptake. This is done through various mechanisms, one of which is the production of bioactive natural products with high chemical diversity. These include terpenoids, alkaloids, non-ribosomal peptides, polyketides and RiPPs. One of the most studied examples is 6-pentyl-2H-pyran-2-one, a volatile organic polyketide, which induces systemic acquired resistance, morphogenesis, and natural product biosynthesis in plants. Methods for culturing Trichoderma spp., isolating and characterising unique bioactive metabolites are discussed here, with an emphasis on dereplication strategies using metabolomics to optimise discovery. In addition, the role of genome mining for the study of natural product biosynthesis in Trichoderma, and more generally, filamentous fungi is discussed. Examples of bioinformatics tools available to date are listed here with applications in Trichoderma and other ascomycetes. New advances in genome engineering in Trichoderma are also detailed, providing insights into available strategies for the validation of biosynthetic gene clusters identified using genome mining. Finally, the use of a combination of omics approaches, namely metabologenomics, is presented as a growing field for natural product discovery in fungi.
{"title":"Advances in the discovery and study of Trichoderma natural products for biological control applications","authors":"Sophie Jin , Fabrizio Alberti","doi":"10.1039/d5np00017c","DOIUrl":"10.1039/d5np00017c","url":null,"abstract":"<div><div>Covering: up to 2025</div></div><div><div>Reducing the prevalence of phytopathogens and their impact on crops is essential to reach sustainable agriculture goals. Synthetic pesticides have been commonly used to control crop disease but are now strongly linked to disease resistance, environmental pollution, depletion of soil biodiversity, and bioaccumulation, leading to adverse effects on human health. As a alternative, the prolific <em>Trichoderma</em> genus has been studied for its biocontrol properties, as well as its ability to promote plant growth and increase nutrient uptake. This is done through various mechanisms, one of which is the production of bioactive natural products with high chemical diversity. These include terpenoids, alkaloids, non-ribosomal peptides, polyketides and RiPPs. One of the most studied examples is 6-pentyl-2<em>H</em>-pyran-2-one, a volatile organic polyketide, which induces systemic acquired resistance, morphogenesis, and natural product biosynthesis in plants. Methods for culturing <em>Trichoderma</em> spp., isolating and characterising unique bioactive metabolites are discussed here, with an emphasis on dereplication strategies using metabolomics to optimise discovery. In addition, the role of genome mining for the study of natural product biosynthesis in <em>Trichoderma</em>, and more generally, filamentous fungi is discussed. Examples of bioinformatics tools available to date are listed here with applications in <em>Trichoderma</em> and other ascomycetes. New advances in genome engineering in <em>Trichoderma</em> are also detailed, providing insights into available strategies for the validation of biosynthetic gene clusters identified using genome mining. Finally, the use of a combination of omics approaches, namely metabologenomics, is presented as a growing field for natural product discovery in fungi.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 8","pages":"Pages 1367-1386"},"PeriodicalIF":10.6,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144232716","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Manyun Chen , Dipesh Dhakal , Campbell W. Eckhardt , Hendrik Luesch , Yousong Ding
Covering: 2014 to 2024
Cyanobacteria are prolific producers of bioactive natural products, including promising drug leads for FDA-approved cancer therapeutics. Advances in genome sequencing and computational tools have revealed a wealth of cyanobacterial biosynthetic gene clusters (BGCs). However, progress in genome-driven discovery has been hindered by challenges in manipulating native hosts and the limited availability of efficient heterologous expression platforms. This highlight focuses on recent synthetic biology innovations on cyanobacterial systems that address these obstacles, facilitating the production of diverse cyanobacterial natural product families. We discuss key features of widely used cyanobacterial chassis, such as Synechocystis sp. PCC 6803, Synechococcus elongatus UTEX 2973, Anabaena sp. PCC 7120, and emerging hosts. Advances in BGC cloning, combinatorial biosynthesis, transcriptional and translational regulation, and host engineering are also highlighted. Together, these synthetic biology developments provide a powerful framework for expanding cyanobacterial natural product discovery and production.
{"title":"Synthetic biology strategies for cyanobacterial systems to heterologously produce cyanobacterial natural products","authors":"Manyun Chen , Dipesh Dhakal , Campbell W. Eckhardt , Hendrik Luesch , Yousong Ding","doi":"10.1039/d5np00009b","DOIUrl":"10.1039/d5np00009b","url":null,"abstract":"<div><div>Covering: 2014 to 2024</div></div><div><div>Cyanobacteria are prolific producers of bioactive natural products, including promising drug leads for FDA-approved cancer therapeutics. Advances in genome sequencing and computational tools have revealed a wealth of cyanobacterial biosynthetic gene clusters (BGCs). However, progress in genome-driven discovery has been hindered by challenges in manipulating native hosts and the limited availability of efficient heterologous expression platforms. This highlight focuses on recent synthetic biology innovations on cyanobacterial systems that address these obstacles, facilitating the production of diverse cyanobacterial natural product families. We discuss key features of widely used cyanobacterial chassis, such as <em>Synechocystis</em> sp. PCC 6803, <em>Synechococcus elongatus</em> UTEX 2973, <em>Anabaena</em> sp. PCC 7120, and emerging hosts. Advances in BGC cloning, combinatorial biosynthesis, transcriptional and translational regulation, and host engineering are also highlighted. Together, these synthetic biology developments provide a powerful framework for expanding cyanobacterial natural product discovery and production.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 8","pages":"Pages 1240-1250"},"PeriodicalIF":10.6,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951908","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Natural product-based research encompasses the discovery, structure elucidation, biosynthesis, synthesis, and application of naturally occurring secondary metabolites. Securingine alkaloids, isolated from Flueggea suffruticosa, have emerged as valuable molecular frameworks for exploring various aspects of natural product research due to their distinct chemical structures, characterized by unique oxidation and rearrangement patterns. Herein, we provide a comprehensive account of our journey in developing novel synthetic strategies and tactics for accessing all known and even unknown securingines and investigating the potential application of securingine B as a novel class of natural product-based molecular photoswitches.
{"title":"Discovery, structure revision, synthesis, and application of all known and even unknown securingine alkaloids","authors":"Chungwoo Lee , Sunkyu Han","doi":"10.1039/d5np00025d","DOIUrl":"10.1039/d5np00025d","url":null,"abstract":"<div><div>Covering: up to 2025</div></div><div><div>Natural product-based research encompasses the discovery, structure elucidation, biosynthesis, synthesis, and application of naturally occurring secondary metabolites. Securingine alkaloids, isolated from <em>Flueggea suffruticosa</em>, have emerged as valuable molecular frameworks for exploring various aspects of natural product research due to their distinct chemical structures, characterized by unique oxidation and rearrangement patterns. Herein, we provide a comprehensive account of our journey in developing novel synthetic strategies and tactics for accessing all known and even unknown securingines and investigating the potential application of securingine B as a novel class of natural product-based molecular photoswitches.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 8","pages":"Pages 1251-1264"},"PeriodicalIF":10.6,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144256861","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Resorcylic acid lactones (RALs) represent a significant category of polyketides characterized by a β-resorcylate unit embedded in a macrolactone ring. Since the discovery of radicicol in 1953, over 300 natural RALs have been identified, showcasing remarkable structural diversity and a wide range of pharmacological activities, including antitumor, antimalarial, antifungal, and immunomodulatory effects. RALs target multiple molecular pathways, such as heat shock protein 90 (HSP90), WNT-5A, pyruvate dehydrogenase kinase 2 (PDK2), mitogen-activated protein kinase (MAPK), and peroxiredoxin 1 (PRDX1). Despite their promising pharmacological profiles, the clinical development of RALs has progressed at a sluggish pace. This review comprehensively catalogs all natural RALs reported to date, explores their bioactivity mechanisms, and critically assesses preclinical and clinical progress. By addressing gaps in mechanistic understanding and translational research, this work highlights the challenges in drug-like properties and clinical applicability, offering valuable insights for future RAL research.
{"title":"The chemical and biological properties of natural resorcylic acid lactones†","authors":"Ying Gao , Wanpeng Li , Hanli Ruan","doi":"10.1039/d5np00033e","DOIUrl":"10.1039/d5np00033e","url":null,"abstract":"<div><div>Covering: 1953 to Feb 2025</div></div><div><div>Resorcylic acid lactones (RALs) represent a significant category of polyketides characterized by a β-resorcylate unit embedded in a macrolactone ring. Since the discovery of radicicol in 1953, over 300 natural RALs have been identified, showcasing remarkable structural diversity and a wide range of pharmacological activities, including antitumor, antimalarial, antifungal, and immunomodulatory effects. RALs target multiple molecular pathways, such as heat shock protein 90 (HSP90), WNT-5A, pyruvate dehydrogenase kinase 2 (PDK2), mitogen-activated protein kinase (MAPK), and peroxiredoxin 1 (PRDX1). Despite their promising pharmacological profiles, the clinical development of RALs has progressed at a sluggish pace. This review comprehensively catalogs all natural RALs reported to date, explores their bioactivity mechanisms, and critically assesses preclinical and clinical progress. By addressing gaps in mechanistic understanding and translational research, this work highlights the challenges in drug-like properties and clinical applicability, offering valuable insights for future RAL research.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 8","pages":"Pages 1387-1410"},"PeriodicalIF":10.6,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144323840","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This review described the total synthesis of naturally occurring cyclic peptides with unique structures covering 2020 to 2022, i.e., darobactin A, pyritide A2, decatransin, mannopeptimycin β, α- and β-amanitins, orfamide A, and MA026, paying particular attention to the construction of their unique structures via macrocyclization.
{"title":"Recent highlights of the total synthesis of cyclic peptide natural products","authors":"Takayuki Doi , Masaya Kumashiro , Kosuke Ohsawa","doi":"10.1039/d4np00056k","DOIUrl":"10.1039/d4np00056k","url":null,"abstract":"<div><div>Covering: 2020 to 2022</div></div><div><div>This review described the total synthesis of naturally occurring cyclic peptides with unique structures covering 2020 to 2022, <em>i.e.</em>, darobactin A, pyritide A2, decatransin, mannopeptimycin β, α- and β-amanitins, orfamide A, and MA026, paying particular attention to the construction of their unique structures <em>via</em> macrocyclization.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 8","pages":"Pages 1265-1275"},"PeriodicalIF":10.6,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144053019","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Atharva S Kulkarni, Guilherme M P Carrara, Jiangpeiyun Jin, Jarrod Laro, Thilini Peramuna, Laura-Isobel McCall, Neha Garg
Covering: 2015 to 2025Chemical crosstalk is universal to all life, niche-specific, and essential to thrive. This crosstalk is mediated by a large diversity of molecules, including metal ions, small molecules, polysaccharides, nucleic acids, lipids, and proteins. Among these, specialized small molecules referred to as natural products (NPs) play an important role in microbe-drug/environment interactions, microbe-microbe, and microbe-host interactions. Microbial communication using NPs allows microbes to sense quorum, form biofilms, eliminate competition, establish symbiosis, evade immune attack, and respond to stress. In most cases, the elucidation of small molecule mediators and effectors of microbe-host interactions presents a major challenge due to the relatively low abundance of microbial metabolites in a milieu of host, microbe, and environmental metabolites. Advances in analytical instrumentation, such as mass spectrometers, and both experimental as well as computational methods to analyze data, coupled with the use of model organisms, have enabled fundamental discoveries of mechanisms of small molecule-mediated host-microbe interactions. The focus of this review is to detail the approaches applied in the last decade to disentangle microbiome-derived NPs in human and murine model systems. Select recent findings from diverse biological ecosystems are discussed to inform relevant parallels and potential strategies for research in human health.
{"title":"Mass spectrometry-based metabolomics approaches to interrogate host-microbiome interactions in mammalian systems.","authors":"Atharva S Kulkarni, Guilherme M P Carrara, Jiangpeiyun Jin, Jarrod Laro, Thilini Peramuna, Laura-Isobel McCall, Neha Garg","doi":"10.1039/d5np00021a","DOIUrl":"10.1039/d5np00021a","url":null,"abstract":"<p><p>Covering: 2015 to 2025Chemical crosstalk is universal to all life, niche-specific, and essential to thrive. This crosstalk is mediated by a large diversity of molecules, including metal ions, small molecules, polysaccharides, nucleic acids, lipids, and proteins. Among these, specialized small molecules referred to as natural products (NPs) play an important role in microbe-drug/environment interactions, microbe-microbe, and microbe-host interactions. Microbial communication using NPs allows microbes to sense quorum, form biofilms, eliminate competition, establish symbiosis, evade immune attack, and respond to stress. In most cases, the elucidation of small molecule mediators and effectors of microbe-host interactions presents a major challenge due to the relatively low abundance of microbial metabolites in a milieu of host, microbe, and environmental metabolites. Advances in analytical instrumentation, such as mass spectrometers, and both experimental as well as computational methods to analyze data, coupled with the use of model organisms, have enabled fundamental discoveries of mechanisms of small molecule-mediated host-microbe interactions. The focus of this review is to detail the approaches applied in the last decade to disentangle microbiome-derived NPs in human and murine model systems. Select recent findings from diverse biological ecosystems are discussed to inform relevant parallels and potential strategies for research in human health.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.6,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12169106/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144300750","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A personal selection of 32 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products, such as shimianolide A from Chloranthus holostegius var. shimianensis.
{"title":"Hot off the Press","authors":"Robert A. Hill and Andrew Sutherland","doi":"10.1039/D5NP90022K","DOIUrl":"10.1039/D5NP90022K","url":null,"abstract":"<p >A personal selection of 32 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products, such as shimianolide A from <em>Chloranthus holostegius</em> var. <em>shimianensis</em>.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" 6","pages":" 945-949"},"PeriodicalIF":10.2,"publicationDate":"2025-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144223779","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Andrew V. Stachulski, Edwin A. Yates, Aleksandra Teriosina, Lesley Hoyles and Simon McArthur
Covering up to 2025.
Plant-derived polyphenols of various chemical classes are widely distributed in dietary substances, e.g. fruits, nuts, vegetables and teas. Such phenolic derivatives are natural antioxidants and have been linked with numerous health benefits, notably anti-cancer and anti-inflammatory properties. Additionally, they may behave as mild estrogens, as in the case of genistein. However, there has often been no clear correlation between in vitro properties, as measured in cell lines for instance, and in vivo performance. Moreover, it is not always clear what the true active species might be, as most phenols are readily subject to phase II metabolism, generating predominantly glucuronides and sulfates. In this highlight, we seek to address the question of whether dietary substance metabolites, especially glucuronides, which have been more widely studied, do indeed possess distinct activities in their own right compared to their parent substances. In most cases this will refer to enzyme inhibition and/or interaction with cell lines. General observations concerning glucuronidation are provided, accompanied by practical comments concerning the synthesis of glucuronides, which are not always available or marketed in useful quantities. The main structural classes of natural polyphenols are introduced, with comments including synthetic details and biological properties for important members of each class.
{"title":"Dietary substances and their glucuronides: structures, occurrence and biological activity","authors":"Andrew V. Stachulski, Edwin A. Yates, Aleksandra Teriosina, Lesley Hoyles and Simon McArthur","doi":"10.1039/D5NP00002E","DOIUrl":"10.1039/D5NP00002E","url":null,"abstract":"<p>Covering up to 2025.</p><p>Plant-derived polyphenols of various chemical classes are widely distributed in dietary substances, <em>e.g.</em> fruits, nuts, vegetables and teas. Such phenolic derivatives are natural antioxidants and have been linked with numerous health benefits, notably anti-cancer and anti-inflammatory properties. Additionally, they may behave as mild estrogens, as in the case of genistein. However, there has often been no clear correlation between <em>in vitro</em> properties, as measured in cell lines for instance, and <em>in vivo</em> performance. Moreover, it is not always clear what the true active species might be, as most phenols are readily subject to phase II metabolism, generating predominantly glucuronides and sulfates. In this highlight, we seek to address the question of whether dietary substance metabolites, especially glucuronides, which have been more widely studied, do indeed possess distinct activities in their own right compared to their parent substances. In most cases this will refer to enzyme inhibition and/or interaction with cell lines. General observations concerning glucuronidation are provided, accompanied by practical comments concerning the synthesis of glucuronides, which are not always available or marketed in useful quantities. The main structural classes of natural polyphenols are introduced, with comments including synthetic details and biological properties for important members of each class.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" 12","pages":" 1924-1935"},"PeriodicalIF":10.6,"publicationDate":"2025-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/np/d5np00002e?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144214409","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Since the Nagoya Protocol came into force in 2014, scientists working with genetic resources have integrated compliance with Access and Benefit-Sharing (ABS) legislation at international and national levels into their research practices. However, two key gaps left by the Nagoya Protocol are being addressed, introducing new obligations for marine natural product scientists: under the auspices of the Convention on Biological Diversity (CBD), a compromise agreement was reached in November 2024 that regulates the use of Digital Sequence Information (DSI) on Genetic Resources. Within the next few years, the 2023 Biodiversity Beyond National Jurisdiction (BBNJ) Agreement is expected to take effect. This treaty covers the access to and use of marine biodiversity of areas beyond national jurisdiction for research and development. In a time when genetic research and marine biodiversity are key to scientific advancement, these evolving policies affect how genetic information is stored, shared, and used, raising emerging questions for the scientific community about their direct impact and the complexities of compliance. Despite continuous developments and scientific community involvement, there remains a notable gap in communication between policy changes and their accessible dissemination to researchers. Addressing this gap is crucial for the continuation of research and the effective use of relevant resources. The main goal of this viewpoint article is to provide a concise guide to recent policy developments relevant to natural product researchers that should be incorporated and harmonized into ongoing scientific activities.
{"title":"Unpacking policy developments in marine natural product research: a scientist's guide to DSI and BBNJ","authors":"Federica Casolari , Amelia Westmoreland , Thomas Vanagt , Marcel Jaspars","doi":"10.1039/d4np00070f","DOIUrl":"10.1039/d4np00070f","url":null,"abstract":"<div><div>Covering: 2014 up to February 2025</div></div><div><div>Since the Nagoya Protocol came into force in 2014, scientists working with genetic resources have integrated compliance with Access and Benefit-Sharing (ABS) legislation at international and national levels into their research practices. However, two key gaps left by the Nagoya Protocol are being addressed, introducing new obligations for marine natural product scientists: under the auspices of the Convention on Biological Diversity (CBD), a compromise agreement was reached in November 2024 that regulates the use of Digital Sequence Information (DSI) on Genetic Resources. Within the next few years, the 2023 Biodiversity Beyond National Jurisdiction (BBNJ) Agreement is expected to take effect. This treaty covers the access to and use of marine biodiversity of areas beyond national jurisdiction for research and development. In a time when genetic research and marine biodiversity are key to scientific advancement, these evolving policies affect how genetic information is stored, shared, and used, raising emerging questions for the scientific community about their direct impact and the complexities of compliance. Despite continuous developments and scientific community involvement, there remains a notable gap in communication between policy changes and their accessible dissemination to researchers. Addressing this gap is crucial for the continuation of research and the effective use of relevant resources. The main goal of this viewpoint article is to provide a concise guide to recent policy developments relevant to natural product researchers that should be incorporated and harmonized into ongoing scientific activities.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 7","pages":"Pages 1063-1070"},"PeriodicalIF":10.6,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143956609","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Cycloaddition of nitrones with alkenes forms isoxazolidines, which are five-membered heterocycles containing nitrogen and oxygen atoms. This transformation functionalizes alkenes by forming C–C and C–O bonds. The N–O bond in the resultant isoxazolidines is easily cleaved. Additionally, when the cycloaddition is carried out intramolecularly, the regioselectivity of the reaction is influenced by the tether connecting the nitrone and alkene and can differ from the selectivity governed by frontier molecular orbital interaction. These features make the intramolecular cycloaddition of nitrones attractive in the synthesis of complex molecules. In this review, we discuss the intramolecular cycloaddition of nitrones used in the total synthesis of natural products.
{"title":"Intramolecular cycloaddition of nitrones in total synthesis of natural products","authors":"Satoshi Yokoshima","doi":"10.1039/d4np00062e","DOIUrl":"10.1039/d4np00062e","url":null,"abstract":"<div><div>Covering 2015 to 2024</div></div><div><div>Cycloaddition of nitrones with alkenes forms isoxazolidines, which are five-membered heterocycles containing nitrogen and oxygen atoms. This transformation functionalizes alkenes by forming C–C and C–O bonds. The N–O bond in the resultant isoxazolidines is easily cleaved. Additionally, when the cycloaddition is carried out intramolecularly, the regioselectivity of the reaction is influenced by the tether connecting the nitrone and alkene and can differ from the selectivity governed by frontier molecular orbital interaction. These features make the intramolecular cycloaddition of nitrones attractive in the synthesis of complex molecules. In this review, we discuss the intramolecular cycloaddition of nitrones used in the total synthesis of natural products.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 7","pages":"Pages 1071-1090"},"PeriodicalIF":10.6,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143584033","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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