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Journal articles on the topic 'Natural Products - Carbocyclic compounds'

Author: Grafiati

Published: 7 September 2023

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1

Banwell, MG. "New Methods for the Synthesis of Troponoid Compounds." Australian Journal of Chemistry 44, no. 1 (1991): 1. http://dx.doi.org/10.1071/ch9910001.

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The ring expansion of 7-halogenobicyclo[4.1.0] heptenones and related compounds provides a useful new method for the preparation of the seven-membered conjugated carbocyclic compounds known as tropones and tropolones. This methodology has been exploited in the synthesis of various biologically active troponoid natural products including nezukone, the thujaplicins, thujaplicinol, MY3-469 and colchicine.

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2

Schmiedel, Volker Martin, and Hans-Ulrich Reissig. "Alkoxyallenes as Starting Materials for the Syntheses of Natural Products." Current Organic Chemistry 23, no. 27 (January 15, 2020): 2976–3003. http://dx.doi.org/10.2174/1385272824666191218115731.

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Alkoxyallenes are easily available and versatile building blocks for the preparation of a variety of natural products (terpenes, polyketides, alkaloids, amino acids, carbohydrates etc.) originating from different classes. The synthetic use of the three allene carbon atoms frequently follows the “normal” reactivity pattern showing that alkoxyallenes can be regarded as special enol ethers. Additions of alcohols or amines to alkoxyallenes form vinyl-substituted O,O- or N,O-acetals that are frequently used in ring-closing metathesis reactions. This methodology delivers crucial heterocyclic units of the target compounds. Enantioselective additions provide products with high enantiopurity. Alternatively, an “Umpolung” of reactivity of alkoxyallenes is achieved by lithiation at C-1 and subsequent reaction with electrophiles, such as alkyl halides, carbonyl compounds, imines or nitrones. High stereoselectivity of the addition step can be achieved by substrate control or auxiliary control. The high diastereo- or enantioselectivity is transferred to the subsequent acyclic or cyclic products. The cyclization of primary addition products occurs efficiently under mild conditions and provides functionalized dihydrofuran, dihydropyrrole or 1,2-oxazine derivatives. These are valuable intermediates for the synthesis of a variety of heterocyclic natural products. Nazarov cyclizations or gold catalyzed rearrangements allow the synthesis of five- and six-membered carbocyclic compounds that are also used for natural product synthesis. Dedicated to Dr. Reinhold Zimmer, a pioneer of alkoxyallene chemistry, on the occasion of his 60th birthday.

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3

Mandal, Sumana, Raju D. Chaudhari, and Goutam Biswas. "Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds." Beilstein Journal of Organic Chemistry 17 (September 9, 2021): 2348–76. http://dx.doi.org/10.3762/bjoc.17.153.

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The synthesis of complex cyclic compounds is extremely challenging for organic chemists. Many transition-metal-salt-mediated cyclizations are reported in literature. Hg(II) salts have been successfully employed in cyclizations to form complex heterocyclic and carbocyclic structures that are impossible to synthesize with other transition metal salts. In this review, we have summarized cyclization reactions that are performed with Hg(II) salts. These salts are also successfully applied in stoichiometric or catalytic amounts to form complex cyclic structures and natural products.

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4

Yan, Ning, Yongmei Du, Xinmin Liu, Hongbo Zhang, Yanhua Liu, and Zhongfeng Zhang. "A Review on Bioactivities of Tobacco Cembranoid Diterpenes." Biomolecules 9, no. 1 (January 16, 2019): 30. http://dx.doi.org/10.3390/biom9010030.

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Cembranoids are carbocyclic diterpenes comprising four isoprene units and are natural products with a parent skeleton consisting of a 14-membered ring. They have gained wide interest in recent years and are a major hotspot in the research of natural product chemistry. Since 1962, various tobacco cembranoid diterpenes have been identified. This review systematically discusses and summarises the excellent antimicrobial, insecticidal, cytotoxic and neuroprotective activities of tobacco cembranoid diterpenes. These compounds show potential to be developed as botanical fungicides, cytotoxic drugs and drugs for the treatment of human immunodeficiency virus, Alzheimer’s disease, Parkinson’s disease, and other neurodegenerative diseases. However, there are relatively few studies on the structure–activity relationship (SAR) of tobacco cembranoid diterpenes. Therefore, future studies should focus on their structural modification, SAR and biogenic relationships.

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Mhaske, Santosh, and Ranjeet Dhokale. "Transition-Metal-Catalyzed Reactions Involving Arynes." Synthesis 50, no. 01 (November 22, 2017): 1–16. http://dx.doi.org/10.1055/s-0036-1589517.

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The plethora of transformations attainable by the transition-metal-catalyzed reactions of arynes has found immense contemporary interest in the scientific community. This review highlights the scope and importance of transition-metal-catalyzed aryne reactions in the field of synthetic organic chemistry reported to date. It covers transformations achieved by the combination of arynes and various transition metals, which provide a facile access to a biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, various heterocycles, and complex natural products.1 Introduction2 Insertion of Arynes3 Annulation of Arynes4 Cycloaddition of Arynes5 Multicomponent Reactions of Arynes6 Miscellaneous Reactions of Arynes7 Total Synthesis of Natural Products Using Arynes8 Conclusion

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6

Chen, Xuefei, Min Xu, Jin Lü, Jianguo Xu, Yemin Wang, Shuangjun Lin, Zixin Deng, and Meifeng Tao. "Biosynthesis of Tropolones inStreptomycesspp.: Interweaving Biosynthesis and Degradation of Phenylacetic Acid and Hydroxylations on the Tropone Ring." Applied and Environmental Microbiology 84, no. 12 (April 13, 2018): e00349-18. http://dx.doi.org/10.1128/aem.00349-18.

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ABSTRACTTropolonoids are important natural products that contain a unique seven-membered aromatic tropolone core and exhibit remarkable biological activities. 3,7-Dihydroxytropolone (DHT) isolated fromStreptomycesspecies is a multiply hydroxylated tropolone exhibiting antimicrobial, anticancer, and antiviral activities. In this study, we determined the DHT biosynthetic pathway by heterologous expression, gene deletion, and biotransformation. Ninetrlgenes and some of the aerobic phenylacetic acid degradation pathway genes (paa) located outside thetrlbiosynthetic gene cluster are required for the heterologous production of DHT. ThetrlAgene encodes a single-domain protein homologous to the C-terminal enoyl coenzyme A (enoyl-CoA) hydratase domain of PaaZ. TrlA truncates the phenylacetic acid catabolic pathway and redirects it toward the formation of heptacyclic intermediates. TrlB is a 3-deoxy-d-arabino-heptulosonic acid-7-phosphate (DAHP) synthase homolog. TrlH is an unusual bifunctional protein bearing an N-terminal prephenate dehydratase domain and a C-terminal chorismate mutase domain. TrlB and TrlH enhancedde novobiosynthesis of phenylpyruvate, thereby providing abundant precursor for the prolific production of DHT inStreptomycesspp. Six seven-membered carbocyclic compounds were identified from thetrlC,trlD,trlE, andtrlFdeletion mutants. Four of these chemicals, including 1,4,6-cycloheptatriene-1-carboxylic acid, tropone, tropolone, and 7-hydroxytropolone, were verified as key biosynthetic intermediates. TrlF is required for the conversion of 1,4,6-cycloheptatriene-1-carboxylic acid into tropone. The monooxygenases TrlE and TrlCD catalyze the regioselective hydroxylations of tropone to produce DHT. This study reveals a natural association of anabolism of chorismate and phenylpyruvate, catabolism of phenylacetic acid, and biosynthesis of tropolones inStreptomycesspp.IMPORTANCETropolonoids are promising drug lead compounds because of the versatile bioactivities attributed to their highly oxidized seven-membered aromatic ring scaffolds. Our present study provides clear insight into the biosynthesis of 3,7-dihydroxytropolone (DHT) through the identification of key genes responsible for the formation and modification of the seven-membered aromatic core. We also reveal the intrinsic mechanism of elevated production of DHT and related tropolonoids inStreptomycesspp. The study on DHT biosynthesis inStreptomycesexhibits a good example of antibiotic production in which both anabolic and catabolic pathways of primary metabolism are interwoven into the biosynthesis of secondary metabolites. Furthermore, our study sets the stage for metabolic engineering of the biosynthetic pathway for natural tropolonoid products and provides alternative synthetic biology tools for engineering novel tropolonoids.

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7

Okumura, Mikiko, and David Sarlah. "Arenophile-Mediated Photochemical Dearomatization of Nonactivated Arenes." CHIMIA International Journal for Chemistry 74, no. 7 (August 12, 2020): 577–83. http://dx.doi.org/10.2533/chimia.2020.577.

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Aromatic compounds are one of the most abundant classes of organic molecules and find utility as precursors for alicyclic hydrocarbon building blocks. While many established dearomatization reactions are exceptionally powerful, dearomatization with concurrent introduction of functionality, i.e. dearomative functionalization, is still a largely underdeveloped field. This review aims to provide an overview of our recent efforts and progress in the development of dearomative functionalization of simple and nonactivated arenes using arenophile-arene cycloaddition platform. These cycloadducts, formed via a visible-light-mediated [4+2]-photocycloaddition, can be elaborated in situ through olefin chemistry or transition-metal-catalyzed ring-opening with carbon-, nitrogen-, and oxygen-based nucleophiles, providing access to diverse structures with functional and stereochemical complexity. Moreover, the dearomatized products are amenable to further elaborations, which effectively install other functionalities onto the resulting alicyclic carbocycles. The utility of the arenophile-mediated dearomatization methods are also highlighted by the facile syntheses of natural products and bioactive compounds through novel disconnections.

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8

Smyrniotopoulos, Vangelis, Anna Cláudia de Andrade Tomaz, Maria de Fátima Vanderlei de Souza, Emídio Vasconcelos Leitão da Cunha, Robert Kiss, Véronique Mathieu, Efstathia Ioannou, and Vassilios Roussis. "Halogenated Diterpenes with In Vitro Antitumor Activity from the Red Alga Sphaerococcus coronopifolius." Marine Drugs 18, no. 1 (December 29, 2019): 29. http://dx.doi.org/10.3390/md18010029.

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Eight new (1–8) structurally diverse diterpenes featuring five different carbocycles were isolated from the organic extracts of the red alga Sphaerococcus coronopifolius collected from the coastline of the Ionian Sea in Greece. The structures of the new natural products, seven of which were halogenated, and the relative configuration of their stereocenters were determined on the basis of comprehensive spectroscopic analyses, including NMR and HRMS data. Compounds 5 and 8 were found to possess in vitro antitumor activity against one murine and five human cancer cell lines with mean IC50 values 15 and 16 μM, respectively.

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9

Tammam, Mohamed A., Lucie Rárová, Marie Kvasnicová, Gabriel Gonzalez, Ahmed M. Emam, Aldoushy Mahdy, Miroslav Strnad, Efstathia Ioannou, and Vassilios Roussis. "Bioactive Steroids from the Red Sea Soft Coral Sinularia polydactyla." Marine Drugs 18, no. 12 (December 10, 2020): 632. http://dx.doi.org/10.3390/md18120632.

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Six new (1, 2, 6, 8, 13, and 20) and twenty previously isolated (3–5, 7, 9–12, 14–19, and 21–26) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral Sinularia polydactyla collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds 3–7, 9–12, 14–20, and 22–26, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids 22 and 23 showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds 11, 12, 22, and 23 at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound 11 exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids 10, 16, and 20 displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds 11 and 23 showed neuroprotective activity on neuron-like SH-SY5Y cells.

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10

Yang, Ji-Min, Yu-Kun Lin, Tao Sheng, Liang Hu, Xin-Pei Cai, and Jin-Quan Yu. "Regio-controllable [2+2] benzannulation with two adjacent C(sp ³ )–H bonds." Science 380, no. 6645 (May 12, 2023): 639–44. http://dx.doi.org/10.1126/science.adg5282.

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Regiocontrol in traditional cycloaddition reactions between unsaturated carbon compounds is often challenging. The increasing focus in modern medicinal chemistry on benzocyclobutene (BCB) scaffolds indicates the need for alternative, more selective routes to diverse rigid carbocycles rich in C(sp 3 ) character. Here, we report a palladium-catalyzed double C–H activation of two adjacent methylene units in carboxylic acids, enabled by bidentate amide-pyridone ligands, to achieve a regio-controllable synthesis of BCBs through a formal [2+2] cycloaddition involving σ bonds only (two C–H bonds and two aryl–halogen bonds). A wide range of cyclic and acyclic aliphatic acids, as well as dihaloheteroarenes, are compatible, generating diversely functionalized BCBs and hetero-BCBs present in drug molecules and bioactive natural products.

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11

Riley, Dean A., Nigel S. Simpkins, and David Moffat. "Synthesis of novel carbocyclic analogues of indolocarbazole natural products." Tetrahedron Letters 40, no. 20 (May 1999): 3929–32. http://dx.doi.org/10.1016/s0040-4039(99)00572-9.

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12

Wright, Austin C., and Brian M. Stoltz. "Enantioselective construction of the tricyclic core of curcusones A–D via a cross-electrophile coupling approach." Chemical Science 10, no. 45 (2019): 10562–65. http://dx.doi.org/10.1039/c9sc04127c.

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13

Chen, Houguang Jeremy, Ronald Hong Xiang Teo, Jonathan Wong, Yongxin Li, Sumod A. Pullarkat, and Pak-Hing Leung. "Challenges in cyclometalation: steric effects leading to competing pathways and η1,η2-cyclometalated iridium(iii) complexes." Dalton Transactions 47, no. 37 (2018): 13046–51. http://dx.doi.org/10.1039/c8dt02639d.

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The iridation of a known cyclometalating ligand led to several products, one of which is an olefin-directed carbocyclic iridacycle. The mechanistic pathways to the formation of these compounds were investigated.

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14

Blunt, John W., Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, and Michèle R. Prinsep. "Marine natural products." Natural Product Reports 33, no. 3 (2016): 382–431. http://dx.doi.org/10.1039/c5np00156k.

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This review of marine natural products for 2014 describes 1378 new compounds and reports structural revisions or assignments of absolute configuration for previously reported compounds. Since 1965 MNP chemists have made ∼9000 collections worldwide yielding ∼25 700 new MNPs. The rate of discovery of MNPs by region is examined in this review.

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15

Blunt, John W., Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, and Michèle R. Prinsep. "Marine natural products." Natural Product Reports 32, no. 2 (2015): 116–211. http://dx.doi.org/10.1039/c4np00144c.

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This review of marine natural products for 2013 describes 1137 new compounds and reports structural revisions and assignments of absolute configurations for previously described compounds. Included is a report of the anticancer sponge metabolite PM060184 that has undergone a remarkably rapid development from discovery in 2005 to the commencement of phase I clinical trials in 2011.

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16

Blunt, John W., Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, and Michèle R. Prinsep. "Marine natural products." Natural Product Reports 34, no. 3 (2017): 235–94. http://dx.doi.org/10.1039/c6np00124f.

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This review of marine natural products for 2015 describes 1340 new compounds and reports structural revisions or assignments of absolute configuration for previously reported compounds. Other aspects of marine natural products research over the three sesquidecades from 1971 are also examined and contrasted against the 2015 discovery of the source of ET-743, also known as the anti-cancer drug Yondelis^®(trabectedin).

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17

Liu, Yuxiao, Yu Liu, Charles S. Shanahan, Xichen Xu, and Michael P. Doyle. "A survey of enoldiazo nucleophilicity in selective C–C bond forming reactions for the synthesis of natural product-like frameworks." Org. Biomol. Chem. 12, no. 28 (2014): 5227–34. http://dx.doi.org/10.1039/c4ob00709c.

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18

Carroll, Anthony R., Brent R. Copp, Rohan A. Davis, Robert A. Keyzers, and Michèle R. Prinsep. "Marine natural products." Natural Product Reports 37, no. 2 (2020): 175–223. http://dx.doi.org/10.1039/c9np00069k.

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19

Aimon, Anthony, Louis J. Farrugia, and J. Stephen Clark. "Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling." Molecules 24, no. 14 (July 22, 2019): 2654. http://dx.doi.org/10.3390/molecules24142654.

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A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a vinylic iodide and an aldehyde. Good yields of carbocyclic products were obtained from the reaction, but diastereomeric mixtures of allylic alcohols were produced. The cyclisation reaction was successful irrespective of the relative configuration of the stereogenic centres in the cyclisation precursor.

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20

Duke, Stephen O., and John Lydon. "Herbicides from Natural Compounds." Weed Technology 1, no. 2 (April 1987): 122–28. http://dx.doi.org/10.1017/s0890037x00029304.

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Phytotoxic compounds from plants and microorganisms represent a wide range of chemistries and mechanisms of action that have potential in the design and development of new herbicides. Although several natural products of higher plants have been patented as herbicides, none have been developed commercially. Many microbial products have been patented as herbicides and several have been or are being developed, including bialophos {L-2-amino-4-[(hydroxy)(methyl)phosphinoyl] -butyryl-L-alanyl-L-alanine} and glufosinate [L-2-amino-4-(hydroxyl)(methyl)(phosphinoyl)-butyric acid]. The new tools of molecular biology and biotechnology are making natural products more attractive alternatives in herbicide discovery programs.

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21

Soós, Tibor, Dániel Horváth, Frigyes Domonyi, Roberta Palkó, and Andrea Lomoschitz. "Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine." Synthesis 50, no. 11 (March 7, 2018): 2181–90. http://dx.doi.org/10.1055/s-0037-1609153.

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A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products.

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22

Arciszewska, Karolina, Anna Pućkowska, Agnieszka Wróbel, and Danuta Drozdowska. "Carbocyclic Analogues of Distamycin and Netropsin." Mini-Reviews in Medicinal Chemistry 19, no. 2 (December 6, 2018): 98–113. http://dx.doi.org/10.2174/1389557518666181009143203.

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The DNA as the depository of genetic information is a natural target for chemotherapy. A lot of anticancer and antimicrobial agents derive their biological activity from their selective interaction with DNA in the minor groove and from their ability to interfere with biological processes such as enzyme catalysis, replication and transcription. The discovery of the details of minor groove binding drugs, such as netropsin and distamycin A, oligoamides built of 4-amino-1-methylpyrrole-2-carboxylic acid residues, allowed to develop various DNA sequence-reading molecules, named lexitropsins, capable of interacting with DNA precisely, strongly and with a high specificity, and at the same time exhibiting significant cytotoxic potential. Among such compounds, lexitropsins built of carbocyclic sixmembered aromatic rings occupy a quite prominent place in drug research. This work is an attempt to present current findings in the study of carbocyclic lexitropins, their structures, syntheses and biological investigations such as DNA-binding and antiproliferative activity.

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23

Cekovic, Zivorad. "Natural products for plant protection." Chemical Industry 60, no. 5-6 (2006): 113–19. http://dx.doi.org/10.2298/hemind0606113c.

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The advantage applying natural products, such as a secondary metabolites, in plant protection is shortly presented. Acceptable solutions for the enhanced ecological criteria, which are requested by the users of pesticides and consumers of agricultural goods, could be the replacement of classical pesticides by natural products in plant protection. Some natural products are already in use as insecticides, herbicides and fungicides because new biotechnological processes, fermentation and biotransformations provide procedures for their industrial production. In addition to biotechnical processes natural compounds possessing pesticide activities are also prepared by chemical synthesis. An active secondary metabolite must first be isolated from natural sauces and then, based on biological toxicological and ecological studies, acceptable compounds are selected for laboratory and industrial chemical synthesis. Several compounds possessing insecticidal, herbicidal and fungicidal activities, which have been successfully applied for plan protection are presented.

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24

Kayser, Oliver, K. Noël Masihi, and Albrecht F. Kiderlen. "Natural products and synthetic compounds as immunomodulators." Expert Review of Anti-infective Therapy 1, no. 2 (July 2003): 319–35. http://dx.doi.org/10.1586/14787210.1.2.319.

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25

Barnes, Jo. "Novel compounds in development from natural products." Inpharma Weekly &NA;, no. 1011 (November 1995): 3–4. http://dx.doi.org/10.2165/00128413-199510110-00003.

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26

Egu, Samuel Attah, Efeturi Abraham Onoabedje, Uchechukwu Chris Okoro, Khalid Mohammed Khan, Abdul Hameed, Irfan Ali, Shafia Iftekhar, Eboh Monday Odin, and Shahbaz Shamim. "The Synthesis and Chemistry of Quinolinediones and their Carbocyclic Analogs." Mini-Reviews in Organic Chemistry 19, no. 5 (August 2022): 591–607. http://dx.doi.org/10.2174/1570193x18666211007120708.

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Abstract: Quinoline-5,8-dione and naphthoquinone nuclei are very important substructures in industrial chemicals and pharmaceuticals. These compounds exhibit a wide variety of activities, including antifungal, antibacterial, antimalarial, antineoplastic, anticoagulant, anticancer, antiviral, radical scavenging, antiplatelet, trypanocidal, cytotoxic, and antineoplastic activities. Currently, several research articles on the importance of many natural and synthetic drugs containing quinolinequinone have been reported. This review covers the progress in quinolinequinone and naphthoquinone chemistry over the last five decades.

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27

Battiste, Merle A., Phillip M. Pelphrey, and Dennis L. Wright. "The Cycloaddition Strategy for the Synthesis of Natural Products Containing Carbocyclic Seven-Membered Rings." Chemistry - A European Journal 12, no. 13 (April 24, 2006): 3438–47. http://dx.doi.org/10.1002/chem.200501083.

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28

Qiu, Rongxiang. "Applications of transition state calculations in the key cyclization of small molecule natural product synthesis." E3S Web of Conferences 290 (2021): 01024. http://dx.doi.org/10.1051/e3sconf/202129001024.

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The diversification of the conformation and configuration of the carbocyclic skeleton of natural products is an important reason for the diversity and complexity of the structure of natural products. The corresponding cyclization synthesis has attracted much attention. Computational chemistry approaches have the advantages of non-toxic, harmless and relatively low cost, and they are increasingly used to model and understand molecular phenomena. The reaction mechanism and thermodynamic parameters determine the feasibility of the cyclization and the enantioselectivity of the cyclization products. The transition state calculations can provide these thermodynamic parameters, which helps to elucidate the cyclization mechanism, calculate the reaction rationality, predict the performance of the new synthesis method and provide a basis for the comprehensive synthesis design.

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29

Eisenreich, Andreas, and Bernd Schäfer. "Natural Compounds in Plant-Based Food." Foods 12, no. 4 (February 17, 2023): 857. http://dx.doi.org/10.3390/foods12040857.

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30

Roberts, S. M., and N. M. Williamson. "The Use of Enzymes for the Preparation of Biologically Active Natural Products and Analogues in Optically Active Form." Current Organic Chemistry 1, no. 1 (May 1997): 1–20. http://dx.doi.org/10.2174/1385272801666220121181731.

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The enantioselective hydrolysis of chiral esters using esterases and lipases gives access to key optically active intermediates en route to prostaglandins, coriolic acid, the anti-HIV agent carbovir and mevinic acid type hypocholestemic agents. The hydrolysis of meso-esters using hydrolases is a very efficient strategy in organic synthesis and has been used to prepare the carbocyclic nucleosides neplanocin and risteromycin. Acylases have been used to prepare (-)-carbovir and both enantiomers of a GABA-mimetic from 2-azabicyclo[2.2.1)hept-5-en-3-one. The employment of nitrilases and nitrile hydratases is gaining in popularity; for example, prochiral 2-benzoyloxypropane-1,3-dinitrile is hydrolysed to (S)-3-benzoyloxy-4-cyanobutanoic acid with exquisite selectivity. Lipases in organic solvents can effect esterification, transesterification and interesterification reactions and this popular methodology has been used to prepare key norcarbocyclic nucleotides and carbocyclic oxetanocin A in single enantiomer form. Yeast catalysed reductions of ketones afford optically active secondary alcohols, typically employed for the synthesis of pheromones, fragrances and chemotactic agents such as leukotriene-84. Instead of a whole-cell system such as yeast, partially purified dehydrogenases can be employed to synthesise (S)-secondary alcohols, for examplan intermediate to the antifungal agent brefeldin-A. Biohydroxylations are important reactions and are being applied to a wide range of substrates. The oxidation of benzene and derivatives to the corresponding cyclohexadiene diols are classic examples and have provided a route to analogues of cyclophellitol. Similarly, mono-oxygenase catalysed Baeyer-Villiger reactions are now well-documented and have furnished intermediates to carbocyclic-AZT, lipoic acid and azadirachtin. Sulfoxides of high optical purity have been prepared by yeast-catalysed oxidation, while enzymes in the transferase and lyase classes have been used to make carbohydrates and amino acids. In conclusion, the science of biotransformations opens up numerous synthetic routes to a wide variety of target molecules that are not easily accessible by other methods of synthetic organic chemistry.

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31

van Santen, Jeffrey A., Ella F. Poynton, Dasha Iskakova, Emily McMann, Tyler A. Alsup, Trevor N. Clark, Claire H. Fergusson, et al. "The Natural Products Atlas 2.0: a database of microbially-derived natural products." Nucleic Acids Research 50, no. D1 (October 28, 2021): D1317—D1323. http://dx.doi.org/10.1093/nar/gkab941.

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Abstract Within the natural products field there is an increasing emphasis on the study of compounds from microbial sources. This has been fuelled by interest in the central role that microorganisms play in mediating both interspecies interactions and host-microbe relationships. To support the study of natural products chemistry produced by microorganisms we released the Natural Products Atlas, a database of known microbial natural products structures, in 2019. This paper reports the release of a new version of the database which includes a full RESTful application programming interface (API), a new website framework, and an expanded database that includes 8128 new compounds, bringing the total to 32 552. In addition to these structural and content changes we have added full taxonomic descriptions for all microbial taxa and have added chemical ontology terms from both NP Classifier and ClassyFire. We have also performed manual curation to review all entries with incomplete configurational assignments and have integrated data from external resources, including CyanoMetDB. Finally, we have improved the user experience by updating the Overview dashboard and creating a dashboard for taxonomic origin. The database can be accessed via the new interactive website at https://www.npatlas.org.

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Wang, Lishu, Jungfeng Wang, Juan Liu, and Yonghong Liu. "Antitubercular Marine Natural Products." Current Medicinal Chemistry 25, no. 20 (June 14, 2018): 2304–28. http://dx.doi.org/10.2174/0929867324666170113120221.

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Due to the importance of nature as a source of new drug candidates, the purpose of this article is to emphasize the marine natural products, which exhibit antitubercular activity, published between January 2000 and May 2016, with 138 quotations to 250 compounds obtained from marine resources. These metabolites are organized by chemical constitution and named as simple alkyl lipids derivatives, aromatics derivatives, peptides, alkaloids, terpenoids, steroids, macrolides, and polycyclic polyketides.

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Ortiz, Aurelio, and Estibaliz Sansinenea. "Macrolactin Antibiotics: Amazing Natural Products." Mini-Reviews in Medicinal Chemistry 20, no. 7 (May 18, 2020): 584–600. http://dx.doi.org/10.2174/1389557519666191205124050.

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The resistance among various microbial species (infectious agents) to different antimicrobial drugs has emerged as a cause of serious public health problem all over the world. In this sense, natural products have been a rich source of compounds for drug discovery with antibiotic activity. Macrolactins are amazing structures which have antibiotic activity against some clinically relevant pathogens. In addition, they have anti-inflammatory, antifungal, antimicrobial, and antitumor activities. They are macrolides containing 24-membered lactone ring with some differences in their chemical structures. The synthesis of these compounds is a difficult task which has attracted attention of researchers; however few syntheses have been reported. In this review, the isolation of all reported macrolactins, their syntheses and biological activities are revisited.

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Reeves, Ryan D., Caitlin N. Kinkema, Eleanor M. Landwehr, Logan E. Vine, and Jennifer M. Schomaker. "Stereodivergent Metal-Catalyzed Allene Cycloisomerizations." Synlett 31, no. 06 (February 4, 2020): 627–31. http://dx.doi.org/10.1055/s-0037-1610746.

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Metal-catalyzed allene cycloisomerizations provide rapid entry into five-membered carbocyclic frameworks, a common motif in natural products and pharmaceuticals. While both Au(I) and Pd(0)-catalyzed allene cycloisomerizations give 5-endo-dig cyclization, Pd prefers the syn diastereomer in contrast to the anti isomer observed with Au. The change in stereoselectivity is proposed to arise from buildup of A1,3 strain during the key carbopalladation step to furnish the cycloisomerized products in moderate to good dr with yields comparable to Au(I) catalysts.

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Rajčević, Nemanja, Danka Bukvički, Tanja Dodoš, and Petar D. Marin. "Interactions between Natural Products—A Review." Metabolites 12, no. 12 (December 14, 2022): 1256. http://dx.doi.org/10.3390/metabo12121256.

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Plant-based natural products have been used as a source for therapeutics since the dawn of civilization. According to the World Health Organization (WHO), more than 80% of the world’s population relies on traditional medicine for their primary healthcare. Numerous natural extracts, widely known in Traditional Chinese Medicine, Indian Ayurveda medicine and other practices, have led to the modern discovery and development of new drugs. Plants continuously interact with their environment, producing new compounds and ever-changing combinations of existing ones. Interestingly, some of the compounds have shown lower therapeutic activity in comparison to the extract they were isolated from. These findings suggest that the higher therapeutic activity of the source extract was due to the synergistic effect of several compounds. In other words, the total therapeutic potential of the extract cannot be explained only by the sum of its parts alone. In traditional medicine, most herbal remedies are based on a mixture of plants, and it is the interaction between different constituents that amplifies their therapeutic potential. Considering the significant influence traditional medicine has on human healthcare, knowing and studying the synergistic effect of compounds is paramount in designing smart therapeutic agents.

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Krivdin, Leonid, and Valentin Semenov. "COMPUTATIONAL NMR OF NATURAL PRODUCTS." Modern Technologies and Scientific and Technological Progress 1, no. 1 (May 17, 2021): 38–39. http://dx.doi.org/10.36629/2686-9896-2021-1-1-38-39.

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A review of the literature data on the calculation of NMR parameters in a large number of natural compounds: alkaloids, terpenes, lactones, lactams, peptides is carried out in order to study their structure, as well as various stereochemical and stereoelectronic effects

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Modugu, Nagi Reddy, and Goverdhan Mehta. "An approach toward novel bioactive natural products antroquinonols: de novo construction of the carbocyclic core." Tetrahedron Letters 56, no. 44 (October 2015): 6030–33. http://dx.doi.org/10.1016/j.tetlet.2015.09.043.

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Haque, Neshatul, Sana Parveen, Tingting Tang, Jiaen Wei, and Zunnan Huang. "Marine Natural Products in Clinical Use." Marine Drugs 20, no. 8 (August 18, 2022): 528. http://dx.doi.org/10.3390/md20080528.

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Marine natural products are potent and promising sources of drugs among other natural products of plant, animal, and microbial origin. To date, 20 drugs from marine sources are in clinical use. Most approved marine compounds are antineoplastic, but some are also used for chronic neuropathic pain, for heparin overdosage, as haptens and vaccine carriers, and for omega-3 fatty-acid supplementation in the diet. Marine drugs have diverse structural characteristics and mechanisms of action. A considerable increase in the number of marine drugs approved for clinical use has occurred in the past few decades, which may be attributed to increasing research on marine compounds in laboratories across the world. In the present manuscript, we comprehensively studied all marine drugs that have been successfully used in the clinic. Researchers and clinicians are hopeful to discover many more drugs, as a large number of marine natural compounds are being investigated in preclinical and clinical studies.

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Maltese, Federica, Frank van der Kooy, and Robert Verpoorte. "Solvent Derived Artifacts in Natural Products Chemistry." Natural Product Communications 4, no. 3 (March 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400326.

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Solvents play an important and critical role in natural product chemistry. They are mainly used during the extraction and purification of metabolites from a biological matrix. To a lesser extent, solvents are also used as reagents or catalysts to perform chemical reactions. This review focuses on the most important classes of solvents, including alcohols, halogen-containing solvents, esters, ethers, acids and bases. The chemical reactions associated with the use of these solvents to form the so-called “artifacts” are discussed and the most common contaminants found in these solvents are also reviewed. The formation of artifacts and the use of contaminated solvents mainly leads to the formation of new compounds, loss of activity of active compounds, formation of active compounds from inactive ones (false positives), loss in total yield of important compounds during isolation, formation of toxic compounds and difficulty in reproducing an extraction or purification method. Finally, the need for stability studies of purified natural products is emphasized, as this is a common overlooked aspect in natural product chemistry.

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Kitamura, Masato, Kengo Miyata, Tomoaki Seki, Namdev Vatmurge, and Shinji Tanaka. "CpRu-catalyzed asymmetric dehydrative allylation." Pure and Applied Chemistry 85, no. 6 (April 15, 2013): 1121–32. http://dx.doi.org/10.1351/pac-con-12-10-02.

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Asymmetric Tsuji–Trost allylation is one of the key chiral technologies for construction of pharmaceutically important compounds because of the high utility of alkenyl-substituted products. Particularly, the dehydrative system using allylic alcohols and protic nucleophiles has started to attract the attention of organic synthetic chemists from the viewpoints of atom and step economy, environmental benignity, and operational simplicity. In this paper, two types of new chiral CpRu catalysts, which have been developed on the basis of redox-mediated donor–acceptor bifunctional catalyst (RDACat) concept, are presented. Complementary use of the chiral catalysts has realized the syntheses of a wide rage of carbocyclic compounds, saturated N- or O-heterocyclic compounds with high reactivity, regioselectivity, enantioselectivity, productivity, and generality.

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Nora De Souza, Marcus Vinícius. "Marine Natural Products Against Tuberculosis." Scientific World JOURNAL 6 (2006): 847–61. http://dx.doi.org/10.1100/tsw.2006.174.

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Natural products represent an outstanding source of compounds that play an important role in the treatment of human diseases. Due to the importance of nature as a source of new drug candidates, the aim of this review is to highlight the marine natural products, which exhibit antituberculosis activity, discovered between 2000 and 2005.

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Laudato, Massimiliano, Luigi Pescitelli, and Raffaele Capasso. "Natural Products of Mineral Origin." Natural Product Communications 8, no. 3 (March 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800336.

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Natural products of mineral origin (alum, bismuth, calcium, magnesium, silicates and zinc compounds) have maintained their popularity as drugs over the course of time. Some evidence still suggests potential benefit of these substances. Therefore, this paper reviews the characteristic features of the respective minerals and their salts along the course of studies on these products.

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Chua, Lee Suan. "Bioactive compounds from natural products with antidiabetic potentials." Longhua Chinese Medicine 5 (March 2022): 1. http://dx.doi.org/10.21037/lcm-21-64.

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Teuten, E. L. "Two Abundant Bioaccumulated Halogenated Compounds Are Natural Products." Science 307, no. 5711 (February 11, 2005): 917–20. http://dx.doi.org/10.1126/science.1106882.

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Khazir, Jabeena, Bilal Ahmad Mir, Shabir Ahmad Mir, and Don Cowan. "Natural products as lead compounds in drug discovery." Journal of Asian Natural Products Research 15, no. 7 (July 2013): 764–88. http://dx.doi.org/10.1080/10286020.2013.798314.

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LU, Jin-Jian, and Yi-Tao WANG. "Identification of anti-cancer compounds from natural products." Chinese Journal of Natural Medicines 18, no. 7 (July 2020): 481–82. http://dx.doi.org/10.1016/s1875-5364(20)30057-1.

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Romano, Barbara, Asif Jilani Iqbal, and Francesco Maione. "Natural Anti-Inflammatory Products/Compounds: Hopes and Reality." Mediators of Inflammation 2015 (2015): 1–2. http://dx.doi.org/10.1155/2015/374239.

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Giles, P. M. "Revised Section F: Natural products and related compounds." Pure and Applied Chemistry 71, no. 4 (January 1, 1999): 587–643. http://dx.doi.org/10.1351/pac199971040587.

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The nomenclature of natural products has suffered from much confusion, mostly for historical reasons. The isolation of a new substance, in the early days of the science, generally preceded its characterization by a lengthy period. Thus, these compounds were often assigned trivial names that gave no indication of the structure of the molecule and were often found afterwards to be misleading. Even when the original names were later revised (for example: glycerin to glycerol) the new names often expressed the structure imperfectly and were thus unsuitable for the nomenclatural manipulation that is required to name derivatives or stereoisomers. The result was a proliferation of trivial names that taxed the memory of chemists and obscured important structural relationships.The resultant disorder in the literature led to the creation of committees of specialists with the task of codifying the naming of compounds in various connected areas of natural-product chemistry, such as steroids, lipids, and carbohydrates. As far as their recommendations have been followed, their efforts have been successful in eliminating confusing or duplicate nomenclature.It is the aim of the lUPAC Commission on Nomenclature of Organic Chemistry to unite as far as possible all the specialist reports into a single set of recommendations that can be applied in most areas of natural-product chemistry. Accordingly, provisional recommendations were prepared and published as Section F of the lUPAC Organic Nomenclature Rules, first in 1976, and then in the 1979 edition of the Rules.

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Parrish, Jonathan D., and R. Daniel Little. "ChemInform Abstract: Natural Products and Medicinally Important Compounds." ChemInform 33, no. 52 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200252273.

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Gallo, Monica. "Extraction and Isolation of Natural Products." Separations 9, no. 10 (October 5, 2022): 287. http://dx.doi.org/10.3390/separations9100287.

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