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Relevant bibliographies by topics / Natural product synthesis / Journal articles

Journal articles on the topic 'Natural product synthesis'

To see the other types of publications on this topic, follow the link: Natural product synthesis.

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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1

Dai, Mingji, Xinpei Cai, and Yu Bai. "Total Syntheses of Spinosyn A." Synlett 29, no. 20 (September 7, 2018): 2623–32. http://dx.doi.org/10.1055/s-0037-1610249.

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Spinosyn A is an important polycyclic natural product with impressive insecticidal activity and has been used worldwide in agriculture as the major component of Spinosad. Herein, four chemical total syntheses of spinosyn A are summarized. Its biosynthesis and a chemoenzymatic total synthesis are discussed as well.1 Biosynthesis2 The Evans Synthesis3 The Paquette Synthesis4 The Roush Synthesis5 The Liu Synthesis6 The Dai Synthesis7 Conclusions

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2

Herzon, Seth B., and Christopher D. Vanderwal. "Introduction: Natural Product Synthesis." Chemical Reviews 117, no. 18 (September 27, 2017): 11649–50. http://dx.doi.org/10.1021/acs.chemrev.7b00520.

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3

Gladysz, J. A. "Introduction: Natural Product Synthesis." Chemical Reviews 105, no. 12 (December 2005): 4235–36. http://dx.doi.org/10.1021/cr0509713.

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4

Martin, Nelson, and Ruchi Bharti. "Arynes in Natural Product Synthesis." International Journal for Research in Applied Science and Engineering Technology 11, no. 4 (April 30, 2023): 2633–44. http://dx.doi.org/10.22214/ijraset.2023.50703.

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Abstract: Arynes are a unique class of intermediates used in synthetic organic chemistry, and research interest has been intensely focused on their peculiar reactivities. Arynes have been researched for almost a century. However, difficulties in monitoring these reactive species, as well as difficulties in creating synthetically viable techniques for their synthesis and trapping, have restricted their application. A key tactic for achieving the racemic and enantiopure total synthesis of a broad variety of natural compounds or their structural derivatives. The chemistry of arynes has advanced significantly over the past thirty years, particularly in the field of transition metal carbon- carbon and carbon-heteroatom bond-forming mechanisms. The field’s fast growth is largely attributable to the development of mild aryne production processes. To create a natural product with complex organic molecules, the role of aryne intermediates was non-replaceable. These organic substances are often used in medicine, therapies, or as raw material for the synthesis of other substances. Moreover, they may perform important biological tasks. There are numerous methods for synthesizing natural compounds including total synthesis, semi-synthesis, and biosynthesis. Total synthesis is the process of creating natural products entirely chemically from basic precursors as well as it can be produced in large quantities and can reveal information about its biological activity. One of the developments in Arynes’ chemistry is the chemical rearrangements brought about by this electrophilic intermediate. It is not feasible to use conventional methods in a single step. This review article discusses how arynes are used to create natural products. Arynes has a wide range of functionality in the field of scientific research. The evolution of this method has made a tremendous change in the total synthesis of natural products. Benzynes enabled creative synthesis in mild conditions. The transformation has expanded to investigate various reaction classes such as nucleophilic addition, (4+2), and (2+2) cycloaddition strategies and metal-catalyzed reactions are shown and explained in this article. This review will provide an idea about how the arynes act as an intermediate in those reaction mechanisms and enlighten the scope of these aryne intermediate.

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5

Vanable, Evan P., Laurel G. Habgood, and James D. Patrone. "Current Progress in the Chemoenzymatic Synthesis of Natural Products." Molecules 27, no. 19 (September 27, 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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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 (August 22, 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

Romero, Kevin J., Matthew S. Galliher, Derek A. Pratt, and Corey R. J. Stephenson. "Radicals in natural product synthesis." Chemical Society Reviews 47, no. 21 (2018): 7851–66. http://dx.doi.org/10.1039/c8cs00379c.

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Free radical intermediates have intrigued chemists since their discovery, and an ever-increasing appreciation for their unique reactivity has resulted in the widespread utilization of these species for natural product synthesis.

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8

Hatakeyama, Susumi. "Fascinated by Natural Product Synthesis." Journal of Synthetic Organic Chemistry, Japan 78, no. 10 (October 1, 2020): 986–89. http://dx.doi.org/10.5059/yukigoseikyokaishi.78.986.

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9

Hetzler, Belinda E., Dirk Trauner, and Andrew L. Lawrence. "Natural product anticipation through synthesis." Nature Reviews Chemistry 6, no. 3 (January 14, 2022): 170–81. http://dx.doi.org/10.1038/s41570-021-00345-7.

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10

Dragutan, Reviewed by Valerian, and Ileana Dragutan. "“Metathesis in Natural Product Synthesis”." Platinum Metals Review 55, no. 1 (January 1, 2011): 33–49. http://dx.doi.org/10.1595/147106711x543190.

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11

Donohoe, Timothy J., Carole J. R. Bataille, and Gwydion H. Churchill. "Highlights of natural product synthesis." Annual Reports Section "B" (Organic Chemistry) 102 (2006): 98. http://dx.doi.org/10.1039/b515095g.

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12

Iriondo-Alberdi, Jone, and Michael F. Greaney. "Photocycloaddition in Natural Product Synthesis." European Journal of Organic Chemistry 2007, no. 29 (October 2007): 4801–15. http://dx.doi.org/10.1002/ejoc.200700239.

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13

Fernandes, Rodney A., Anupama Kumari, and Ramdas S. Pathare. "A Decade with Dötz Benzannulation in the Synthesis of Natural Products." Synlett 31, no. 05 (February 3, 2020): 403–20. http://dx.doi.org/10.1055/s-0039-1690791.

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The Dötz benzannulation is a named reaction that utilizes Fischer chromium carbenes in a formal [3+2+1] cycloaddition with an alkyne and CO to produce the corresponding benzannulated product. Since its development in the 1970s, this reaction has been extensively used in the synthesis of natural products and various molecular architectures. Although the reaction sometimes suffers from the formation of other competing side products, the rapid construction of naphthol structures with a 1,4-dihydroxy unit makes it the most appropriate reaction for the synthesis of p-naphthoquinones. This review focuses on our group’s efforts over the past decade on the extensive use of this annulation reaction along with the contributions of others on the synthesis of different natural products.1 Introduction2 General Description and Mechanism of the Dötz Benzannulation Reaction3 Applications of the Dötz Benzannulation in Natural Product Synthesis over the Last Decade4 Conclusion

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14

Beemelmanns, Christine, Dávid Roman, and Maria Sauer. "Applications of the Horner–Wadsworth–Emmons Olefination in Modern Natural Product Synthesis." Synthesis 53, no. 16 (April 28, 2021): 2713–39. http://dx.doi.org/10.1055/a-1493-6331.

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AbstractThe Horner–Wadsworth–Emmons (HWE) reaction is one of the most reliable olefination reaction and can be broadly applied in organic chemistry and natural product synthesis with excellent selectivity. Within the last few years HWE reaction conditions have been optimized and new reagents developed to overcome challenges in the total syntheses of natural products. This review highlights the application of HWE olefinations in total syntheses of structurally different natural products covering 2015 to 2020. Applied HWE reagents and reactions conditions are highlighted to support future synthetic approaches and serve as guideline to find the best HWE conditions for the most complicated natural products.1 Introduction and Historical Background2 Applications of HWE2.1 Cyclization by HWE Reactions2.2.1 Formation of Medium- to Larger-Sized Rings2.2.2 Formation of Small- to Medium-Sized Rings2.3 Synthesis of α,β-Unsaturated Carbonyl Groups2.4 Synthesis of Substituted C=C Bonds2.5 Late-Stage Modifications by HWE Reactions2.6 HWE Reactions on Solid Supports2.7 Synthesis of Poly-Conjugated C=C Bonds2.8 HWE-Mediated Coupling of Larger Building Blocks2.9 Miscellaneous3 Summary and Outlook

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15

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 (February 3, 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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16

Davies, Huw M. L., Kenichiro Itami, and Brian M. Stoltz. "New directions in natural product synthesis." Chemical Society Reviews 47, no. 21 (2018): 7828–29. http://dx.doi.org/10.1039/c8cs90115e.

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17

Hui, Chunngai, Zhuo Wang, Shiping Wang, and Chunfa Xu. "Molecular editing in natural product synthesis." Organic Chemistry Frontiers 9, no. 5 (2022): 1451–57. http://dx.doi.org/10.1039/d2qo00043a.

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18

Wang, Dan, and Shuanhu Gao. "Sonogashira coupling in natural product synthesis." Org. Chem. Front. 1, no. 5 (2014): 556–66. http://dx.doi.org/10.1039/c3qo00086a.

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19

Moore, Bradley S., and Tobias A. M. Gulder. "Enzymes in natural product total synthesis." Natural Product Reports 37, no. 10 (2020): 1292–93. http://dx.doi.org/10.1039/d0np90038a.

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20

Ando, Yoshio. "Photochemical Reactions in Natural Product Synthesis." Journal of Synthetic Organic Chemistry, Japan 68, no. 10 (2010): 1067–68. http://dx.doi.org/10.5059/yukigoseikyokaishi.68.1067.

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21

Yamaguchi, Junichiro. "Natural Product Synthesis: 30 Years Later." Journal of Synthetic Organic Chemistry, Japan 76, no. 5 (May 1, 2018): 510–13. http://dx.doi.org/10.5059/yukigoseikyokaishi.76.510.

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22

Narquizian, Robert, Jacqueline Mine, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (2000): ix—xi. http://dx.doi.org/10.1039/b003116j.

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23

Narquizian, Robert, Jacqueline Milne, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 14 (2000): ix—xii. http://dx.doi.org/10.1039/b004204h.

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24

McArthur, Duncan, and Jacqueline Milne. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 16 (2000): xxii—xxv. http://dx.doi.org/10.1039/b004801l.

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25

Milne, Jacqueline E., Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 18 (2000): xv—xviii. http://dx.doi.org/10.1039/b006702o.

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26

Milne, Jaqueline E., Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 20 (2000): xv—xx. http://dx.doi.org/10.1039/b007693g.

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27

Narquizian, Robert. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (2000): ix—xiv. http://dx.doi.org/10.1039/b000126k.

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28

Narquizian, Robert, and Jacqueline Milne. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (2000): xi—xvi. http://dx.doi.org/10.1039/b000732n.

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29

Narquizian, Robert, and Jacqueline Milne. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (2000): 10—ix. http://dx.doi.org/10.1039/b001652m.

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30

Narquizian, Robert, and Jacqueline Milne. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 8 (2000): vii—x. http://dx.doi.org/10.1039/b001753l.

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31

Narquizian, Robert, and Emma Guthrie. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (1999): ix—xiv. http://dx.doi.org/10.1039/a907858d.

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32

Narquizian, Robert, and Jens Kaufmann. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (1999): xvii—xx. http://dx.doi.org/10.1039/a908808c.

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33

Gunn, Andrew, Jacqueline E. Milne, Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (2001): 2–5. http://dx.doi.org/10.1039/b109682f.

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34

Gunn, Andrew, Jacqueline E. Milne, Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (2001): ix. http://dx.doi.org/10.1039/b200355b.

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35

Gunn, Andrew, Jacqueline E. Milne, Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 5 (2001): xi. http://dx.doi.org/10.1039/b201458k.

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36

Anderson, Edward A. "Cascade polycyclisations in natural product synthesis." Organic & Biomolecular Chemistry 9, no. 11 (2011): 3997. http://dx.doi.org/10.1039/c1ob05212h.

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37

Gunn, Andrew, Stephen McAteer, Jacqueline E. Milne, and Marcel de Puit. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (2002): ix. http://dx.doi.org/10.1039/b204498f.

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38

Gunn, Andrew, Stephen McAteer, Jacqueline E. Milne, and Marcel de Puit. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 14 (2001): x. http://dx.doi.org/10.1039/b205788n.

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39

Gunn, Andrew, Stephen McAteer, Jacqueline E. Milne, and Marcel de Puit. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (2001): vii. http://dx.doi.org/10.1039/b206710m.

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40

Gunn, Andrew, Stephen McAteer, Jacqueline E. Milne, and Marcel de Puit. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 17 (August 23, 2002): vii. http://dx.doi.org/10.1039/b207912g.

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41

Gunn, Andrew, Jacqueline E. Milne, Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (2001): xv—xix. http://dx.doi.org/10.1039/b103457j.

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42

Gunn, Andrew, Jacqueline E. Milne, Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (2001): xvi—xix. http://dx.doi.org/10.1039/b104270j.

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43

Gunn, Andrew, Jacqueline E. Milne, Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 14 (2001): xv—xviii. http://dx.doi.org/10.1039/b105193h.

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44

Gunn, Andrew, Jacqueline E. Milne, Marcel de Puit, and Duncan McArthur. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 16 (2001): xiii—xvi. http://dx.doi.org/10.1039/b106740k.

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45

Narquizian, Robert, and Emma Guthrie. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (1999): 833–38. http://dx.doi.org/10.1039/a901858a.

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46

Narquizian, Robert, and Emma Guthrie. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (1999): ix—xiv. http://dx.doi.org/10.1039/a903364e.

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47

Narquizian, Robert, and Emma Guthrie. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (1999): ix—xii. http://dx.doi.org/10.1039/a903366a.

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48

Narquizian, Robert, and Emma Guthrie. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 14 (1999): ix—xiii. http://dx.doi.org/10.1039/a904288a.

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49

Narquizian, Robert, and Emma Guthrie. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 16 (1999): ix—xiv. http://dx.doi.org/10.1039/a905504e.

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50

Narquizian, Robert, and Emma Guthrie. "Perkin 1 Abstracts: Natural Product Synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 18 (1999): xi—xiv. http://dx.doi.org/10.1039/a905954g.

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