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Journal articles on the topic 'Natural products – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Fay, Nicolas, Rémi Blieck, Cyrille Kouklovsky, and Aurélien de la Torre. "Total synthesis of grayanane natural products." Beilstein Journal of Organic Chemistry 18 (December 12, 2022): 1707–19. http://dx.doi.org/10.3762/bjoc.18.181.

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Grayananes are a broad family of diterpenoids found in Ericaceae plants, comprising more than 160 natural products. Most of them exhibit interesting biological activities, often representative of Ericaceae use in traditional medicine. Over the last 50 years, various strategies were described for the total synthesis of these diterpenoids. In this review, we survey the literature for synthetic approaches to access grayanane natural products. We will focus mainly on completed total syntheses, but will also mention unfinished synthetic efforts. This work aims at providing a critical perspective on grayanane synthesis, highlighting the advantages and downsides of each strategy, as well as the challenges remaining to be tackled.

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2

ROUHI, MAUREEN. "SYNTHESIS OF NATURAL PRODUCTS." Chemical & Engineering News 74, no. 45 (1996): 6–7. http://dx.doi.org/10.1021/cen-v074n045.p006.

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3

Kishi, Y. "Natural products synthesis: palytoxin." Pure and Applied Chemistry 61, no. 3 (1989): 313–24. http://dx.doi.org/10.1351/pac198961030313.

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4

Yokoshima, Satoshi. "Synthesis of Polycyclic Natural Products through Skeletal Rearrangement." Synlett 31, no. 20 (2020): 1967–75. http://dx.doi.org/10.1055/s-0040-1707904.

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Construction of rings through reliable reactions followed by changes in the ring size or the connectivity through skeletal rearrangement provides molecules with a wide range of skeletons. In this account, our syntheses of polycyclic natural products through skeletal rearrangement are discussed.1 Introduction2 Synthesis through Changes in the Ring Size3 Synthesis by Biomimetic Strategies4 Synthesis through Metathesis5 Synthesis through Temporary Formation of a Ring6 Conclusion

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5

Nicolaou, K. C., and Jason S. Chen. "Total synthesis of complex heterocyclic natural products." Pure and Applied Chemistry 80, no. 4 (2008): 727–42. http://dx.doi.org/10.1351/pac200880040727.

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Total synthesis campaigns toward complex heterocyclic natural products are a prime source of inspiration for the design and execution of complex cascade sequences, powerful reactions, and efficient synthetic strategies. We highlight selected examples of such innovations in the course of our total syntheses of diazonamide A, azaspiracid-1, thiostrepton, 2,2'-epi-cytoskyrin A and rugulosin, abyssomycin C, platensimycin, and uncialamycin.

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6

Hou, Si-Hua, Feng-Fan Zhou, Yi-Hang Sun, and Quan-Zhe Li. "Deconstructive and Divergent Synthesis of Bioactive Natural Products." Molecules 28, no. 17 (2023): 6193. http://dx.doi.org/10.3390/molecules28176193.

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Natural products play a key role in innovative drug discovery. To explore the potential application of natural products and their analogues in pharmacology, total synthesis is a key tool that provides natural product candidates and synthetic analogues for drug development and potential clinical trials. Deconstructive synthesis, namely building new, challenging structures through bond cleavage of easily accessible moieties, has emerged as a useful design principle in synthesizing bioactive natural products. Divergent synthesis, namely synthesizing many natural products from a common intermediate, can improve the efficiency of chemical synthesis and generate libraries of molecules with unprecedented structural diversity. In this review, we will firstly introduce five recent and excellent examples of deconstructive and divergent syntheses of natural products (2021–2023). Then, we will summarize our previous work on the deconstructive and divergent synthesis of natural products to demonstrate the high efficiency and simplicity of these two strategies in the field of total synthesis.

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7

Ortiz, Aurelio, and Estibaliz Sansinenea. "Macrolactin Antibiotics: Amazing Natural Products." Mini-Reviews in Medicinal Chemistry 20, no. 7 (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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8

Diez, David. "Catalyzed Synthesis of Natural Products." Catalysts 9, no. 11 (2019): 884. http://dx.doi.org/10.3390/catal9110884.

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9

Pouységu, Laurent, Denis Deffieux, Gaëlle Malik, Anna Natangelo, and Stéphane Quideau. "Synthesis of ellagitannin natural products." Natural Product Reports 28, no. 5 (2011): 853. http://dx.doi.org/10.1039/c0np00058b.

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10

Koskinen, Ari M. P., and Atta-ur-rahman. "Asymmetric Synthesis of Natural Products." Natural Product Letters 4, no. 1 (1994): 79. http://dx.doi.org/10.1080/10575639408043896.

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11

Nielsen, John. "Combinatorial synthesis of natural products." Current Opinion in Chemical Biology 6, no. 3 (2002): 297–305. http://dx.doi.org/10.1016/s1367-5931(02)00330-7.

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12

Aitken, R. Alan. "Asymmetric Synthesis of Natural Products." Synthesis 1994, no. 01 (1994): 121–22. http://dx.doi.org/10.1055/s-1994-25419.

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13

Dinh, T. H. "Asymmetric synthesis of natural products." Biochimie 75, no. 11 (1993): 1022. http://dx.doi.org/10.1016/0300-9084(93)90162-l.

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14

Huang, Gangliang, Xueqin Zhang, Min Li, Ping Li, Deqi Luo, and Zhangmei Liu. "Synthesis of Glycosylated Natural Products." Current Organic Synthesis 11, no. 6 (2014): 874–78. http://dx.doi.org/10.2174/1570179411666140812233904.

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15

Liu, Wan-Hwa, and Hsien-Jen Wu. "Synthesis of Furanoid Natural Products." Journal of the Chinese Chemical Society 35, no. 3 (1988): 241–46. http://dx.doi.org/10.1002/jccs.198800036.

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16

Heasley, Brian. "Synthesis of Limonoid Natural Products." European Journal of Organic Chemistry 2011, no. 1 (2010): 19–46. http://dx.doi.org/10.1002/ejoc.201001218.

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17

Vanable, Evan P., Laurel G. Habgood, and James D. Patrone. "Current Progress in the Chemoenzymatic Synthesis of Natural Products." Molecules 27, no. 19 (2022): 6373. http://dx.doi.org/10.3390/molecules27196373.

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Natural products, with their array of structural complexity, diversity, and biological activity, have inspired generations of chemists and driven the advancement of techniques in their total syntheses. The field of natural product synthesis continuously evolves through the development of methodologies to improve stereoselectivity, yield, scalability, substrate scope, late-stage functionalization, and/or enable novel reactions. One of the more interesting and unique techniques to emerge in the last thirty years is the use of chemoenzymatic reactions in the synthesis of natural products. This review highlights some of the recent examples and progress in the chemoenzymatic synthesis of natural products from 2019–2022.

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18

Chakrabarty, Suman, Evan O. Romero, Joshua B. Pyser, Jessica A. Yazarians, and Alison R. H. Narayan. "Chemoenzymatic Total Synthesis of Natural Products." Accounts of Chemical Research 54, no. 6 (2021): 1374–84. http://dx.doi.org/10.1021/acs.accounts.0c00810.

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19

Dickschat, Jeroen S. "Natural products in synthesis and biosynthesis." Beilstein Journal of Organic Chemistry 9 (September 19, 2013): 1897–98. http://dx.doi.org/10.3762/bjoc.9.223.

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20

Umezawa, Taiki, Keisuke Nishikawa, Tatsufumi Okino, and Fuyuhiko Matsuda. "Total Synthesis of Natural Antifouling Products." Journal of Synthetic Organic Chemistry, Japan 74, no. 7 (2016): 689–99. http://dx.doi.org/10.5059/yukigoseikyokaishi.74.689.

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21

Scott, A. Ian. "Genetically Engineered Synthesis of Natural Products." Journal of Natural Products 57, no. 5 (1994): 557–73. http://dx.doi.org/10.1021/np50107a001.

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22

Pihko, Ainoliisa J., and Ari M. P. Koskinen. "Synthesis of propellane-containing natural products." Tetrahedron 61, no. 37 (2005): 8769–807. http://dx.doi.org/10.1016/j.tet.2005.06.013.

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23

Donaldson, William A. "Synthesis of cyclopropane containing natural products." Tetrahedron 57, no. 41 (2001): 8589–627. http://dx.doi.org/10.1016/s0040-4020(01)00777-3.

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24

Gung, Benjamin W. "Total synthesis of polyyne natural products." Comptes Rendus Chimie 12, no. 3-4 (2009): 489–505. http://dx.doi.org/10.1016/j.crci.2008.08.014.

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25

Shoji, Mitsuru. "Total Synthesis of Epoxyquinonoid Natural Products." Bulletin of the Chemical Society of Japan 80, no. 9 (2007): 1672–90. http://dx.doi.org/10.1246/bcsj.80.1672.

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26

Scott, A. I. "Genetically engineered synthesis of natural products." Pure and Applied Chemistry 65, no. 6 (1993): 1299–308. http://dx.doi.org/10.1351/pac199365061299.

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27

Kende, A. S. "Rearrangement strategies in natural products synthesis." Pure and Applied Chemistry 69, no. 3 (1997): 407–12. http://dx.doi.org/10.1351/pac199769030407.

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28

Nicolaou, K. C., and E. W. Yue. "Total synthesis of selected natural products." Pure and Applied Chemistry 69, no. 3 (1997): 413–18. http://dx.doi.org/10.1351/pac199769030413.

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29

Hernandez, Lucas W., and David Sarlah. "Empowering Synthesis of Complex Natural Products." Chemistry – A European Journal 25, no. 58 (2019): 13248–70. http://dx.doi.org/10.1002/chem.201901808.

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30

Nasir, Shah Bakhtiar, Noorsaadah Abd Rahman, and Chin Fei Chee. "Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review." Current Organic Synthesis 15, no. 2 (2018): 221–29. http://dx.doi.org/10.2174/1570179414666170821120234.

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Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

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31

Takao, Ken-ichi, Akihiro Ogura, Keisuke Yoshida, and Siro Simizu. "Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions." Synlett 31, no. 05 (2020): 421–33. http://dx.doi.org/10.1055/s-0039-1691580.

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In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.1 Introduction2 Total Synthesis of (+)-Pestalotiopsin A3 Total Synthesis of (+)-Cytosporolide A4 Total Synthesis of (+)-Vibsanin A5 Total Syntheses of (+)-Aquatolide and Related Humulanolides6 Conclusion

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32

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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33

Anderson, Zoe J., and David J. Fox. "Total synthesis of the azolemycins." Organic & Biomolecular Chemistry 14, no. 4 (2016): 1450–54. http://dx.doi.org/10.1039/c5ob02520f.

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34

Norcott, P., and C. S. P. McErlean. "Synthesis of carbazoloquinone natural products ‘on-water’." Organic & Biomolecular Chemistry 13, no. 24 (2015): 6866–78. http://dx.doi.org/10.1039/c5ob00852b.

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35

Eggert, Alina, Christoph Etling, Dennis Lübken, Marius Saxarra, and Markus Kalesse. "Contiguous Quaternary Carbons: A Selection of Total Syntheses." Molecules 25, no. 17 (2020): 3841. http://dx.doi.org/10.3390/molecules25173841.

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Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses of natural products that exhibit a dense assembly of quaternary carbons and whose syntheses were uncompleted until recently. While discussing their syntheses, we not only cover the most recent total syntheses but also provide an update on the status quo of modern syntheses of complex natural products. Herein, we review (±)-canataxpropellane, (+)-waihoensene, (–)-illisimonin A and (±)-11-O-debenzoyltashironin as prominent examples of natural products bearing contiguous quaternary carbons.

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36

Miyashita, Masaaki. "Recent progress in the synthesis of bioactive polycyclic natural products." Pure and Applied Chemistry 79, no. 4 (2007): 651–65. http://dx.doi.org/10.1351/pac200779040651.

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The zoanthamine alkaloids, a type of heptacyclic marine alkaloid isolated from colonial zoanthids of the genus Zoanthus sp., have distinctive biological and pharmacological properties as well as their unique chemical structures with stereochemical complexity. Namely, norzoanthamine can suppress the loss of bone weight and strength in ovariectomized mice and has been considered a promising candidate for an antiosteoporotic drug, whereas zoanthamine has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects. Recently, norzoanthamine derivatives were demonstrated to inhibit strongly the growth of P-388 murine leukemia cell lines, in addition to their potent antiplatelet activities on human platelet aggregation. These distinctive biological properties, combined with novel chemical structures, make this family of alkaloids extremely attractive targets for chemical synthesis. However, the chemical synthesis of the zoanthamine alkaloids has been impeded owing to their densely fuctionalized complex stereostructures. We report here the first and highly stereoselective total syntheses of norzoanthamine and zoanthamine, which involves stereoselective synthesis of the requisite triene for intramolecular Diels-Alder reaction via three-component coupling reactions, a key intramolecular Diels-Alder reaction, and subsequent crucial bis-aminoacetalization as the key steps.

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37

Maliakel, Balu P., and Walther Schmid. "Chemo-enzymatic synthesis of natural products: synthesis of sphydrofuran." Tetrahedron Letters 33, no. 23 (1992): 3297–300. http://dx.doi.org/10.1016/s0040-4039(00)92071-9.

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38

Baron, Anne, Matthew Ball, Benjamin Bradshaw, et al. "Approaches to the stereoselective total synthesis of biologically active natural products." Pure and Applied Chemistry 77, no. 1 (2005): 103–17. http://dx.doi.org/10.1351/pac200577010103.

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Total syntheses of epothilone B and pamamycin 607, which feature reactions between functionalized allylstannanes and aldehydes to introduce a (Z)-trisubstituted double-bond and remote stereocenters stereoselectively, are discussed. Recent work concerned with carrying out this chemistry without the use of allylstannanes as starting materials and progress toward a total synthesis of bryostatins are also presented.

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39

Taniguchi, Tsuyoshi, and Hiroyuki Ishibashi. "Synthesis of Natural Products Using Radical Cascades." Journal of Synthetic Organic Chemistry, Japan 71, no. 3 (2013): 229–36. http://dx.doi.org/10.5059/yukigoseikyokaishi.71.229.

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40

Minami, Atsushi, and Hideaki Oikawa. "Synthesis of Natural Products with Biosynthetic Machinery." Journal of Synthetic Organic Chemistry, Japan 72, no. 5 (2014): 548–56. http://dx.doi.org/10.5059/yukigoseikyokaishi.72.548.

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41

Hattori, Hiromu. "Biocatalyst Aided Total Synthesis of Natural Products." Journal of Synthetic Organic Chemistry, Japan 76, no. 12 (2018): 1358–59. http://dx.doi.org/10.5059/yukigoseikyokaishi.76.1358.

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42

Watanabe, Takumi. "Synthesis of Caprazamycins and Related Natural Products." HETEROCYCLES 95, no. 2 (2017): 662. http://dx.doi.org/10.3987/rev-16-sr(s)5.

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43

Kelecom, Alphonse. "Synthesis of Marine Natural Products in Brazil." Journal of the Brazilian Chemical Society 9, no. 2 (1998): 101–18. http://dx.doi.org/10.1590/s0103-50531998000200002.

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44

Dickschat, Jeroen S. "Natural products in synthesis and biosynthesis II." Beilstein Journal of Organic Chemistry 12 (March 3, 2016): 413–14. http://dx.doi.org/10.3762/bjoc.12.44.

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45

Donner, Christopher, Melvyn Gill, and Leonie Tewierik. "Synthesis of Pyran and Pyranone Natural Products." Molecules 9, no. 6 (2004): 498–512. http://dx.doi.org/10.3390/90600498.

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46

KATOH, Tadashi. "Total Synthesis of Biologically Active Natural Products." Journal of Pesticide Science 25, no. 4 (2000): 446–50. http://dx.doi.org/10.1584/jpestics.25.446.

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47

Qin, Zhiwei, Sheng Huang, Yi Yu, and Hai Deng. "Dithiolopyrrolone Natural Products: Isolation, Synthesis and Biosynthesis." Marine Drugs 11, no. 10 (2013): 3970–97. http://dx.doi.org/10.3390/md11103970.

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48

Yokoshima, Satoshi. "Synthesis of Natural Products with Polycyclic Systems." Chemical and Pharmaceutical Bulletin 61, no. 3 (2013): 251–57. http://dx.doi.org/10.1248/cpb.c12-01031.

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49

Lindel, Thomas, and Fabia Hentschel. "Synthesis of Oximinotyrosine-Derived Marine Natural Products." Synthesis 2010, no. 02 (2009): 181–204. http://dx.doi.org/10.1055/s-0029-1218615.

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50

Pyser, Joshua B., Summer A. Baker Dockrey, Attabey Rodríguez Benítez, et al. "Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products." Journal of the American Chemical Society 141, no. 46 (2019): 18551–59. http://dx.doi.org/10.1021/jacs.9b09385.

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