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Journal articles on the topic 'Organic chemistry ; Natural products ; natural product synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Wang, Zhuo, and Junyang Liu. "All-carbon [3 + 2] cycloaddition in natural product synthesis." Beilstein Journal of Organic Chemistry 16 (December 9, 2020): 3015–31. http://dx.doi.org/10.3762/bjoc.16.251.

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Many natural products possess interesting medicinal properties that arise from their intriguing chemical structures. The highly-substituted carbocycle is one of the most common structural features in many structurally complicated natural products. However, the construction of highly-substituted, stereo-congested, five-membered carbocycles containing all-carbon quaternary center(s) is, at present, a distinct challenge in modern synthetic chemistry, which can be accessed through the all-carbon [3 + 2] cycloaddition. More importantly, the all-carbon [3 + 2] cycloaddition can forge vicinal all-carbon quaternary centers in a single step and has been demonstrated in the synthesis of complex natural products. In this review, we present the development of all-carbon [3 + 2] cycloadditions and illustrate their application in natural product synthesis reported in the last decade covering 2011–2020 (inclusive).

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2

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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3

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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4

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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5

Ball, Philip. "Synthetic organic chemistry in China: building on an ancient tradition—an interview with Qi-Lin Zhou and Xiaoming Feng." National Science Review 4, no. 3 (April 4, 2017): 437–40. http://dx.doi.org/10.1093/nsr/nwx035.

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Abstract If the core of chemistry is making molecules, then the construction of those found in nature—natural products—has long been regarded as one of the highest forms of the art in synthesis. These molecules, produced by living organisms for a variety of purposes, are a key source of pharmaceuticals such as antibiotics and anticancer agents. The medicinal value of natural products has been known for centuries via herbal treatments, and such compounds are still collected, refined and screened for potential drugs today, sometimes being identified from local ‘folk medicine’ practices. By identifying the active ingredients of natural extracts used in traditional medicine, chemists can then synthesize modified forms that may be even more active: this was how the analgesic aspirin was first identified as a derivative of the plant hormone salicylic acid from willow bark. As well as offering such derivatives, natural-product synthesis in organic chemistry can potentially provide a more plentiful alternative source of natural products that are available in only tiny amounts from their natural sources. Efforts to devise cheap and efficient synthetic strategies for molecules such as paclitaxel (Taxol, an anticancer agent present in the Pacific yew) and artemisinin (an anti-malarial extracted from the herb sweet wormwood, qinghao (青蒿), and recognized by the 2015 Nobel Prize for Medicine) are still on-going to satisfy global demand. Organic synthesis is about much more than making natural products: it contributes, for example, to catalysis, polymer chemistry, food science and the development of wholly synthetic drugs. Yet efforts to make complex natural products may supply a motivational testing ground for developing new synthetic techniques with broader applications. Indeed, many chemists prize the discovery of a new synthetic method above the recreation of some complex natural molecule: it is the means, not the end, that matters. The field of organic and natural-product synthesis has a strong history in China, where there is a long tradition of herbal medicine. The use of the qinghao extract for treating malaria is first recorded in AD 340, in a manual that the 2015 Nobel laureate Tu Youyou says she consulted for clues about isolating the compound in the beginning of 1970s. Some say that, in the past decade, Chinese natural-product chemistry has entered a ‘golden era’ (Zheng Q-Y and Li A. Sci China Chem 2016;59: 1059–60). Qi-Lin Zhou of Nankai University and Xiaoming Feng of Sichuan University have been at the forefront of this upsurge. Both of them have developed methods for making so-called chiral molecules: arrangements of atoms that have a handedness, so that they can exist in two mirror-image versions. Natural products typically are chiral molecules, and their biological activity may depend on having the correct handedness. The selective synthesis of chiral molecules (asymmetric synthesis) is therefore vital to natural-product chemistry, and typically involves the use of catalysts that are chiral themselves. National Science Review spoke to Zhou and Feng about their work and their perspectives on organic synthesis in China. Qi-Lin Zhou of College of Chemistry at Nankai University, China. (Courtesy of Q Zhou)

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6

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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7

Speck, Klaus, and Thomas Magauer. "The chemistry of isoindole natural products." Beilstein Journal of Organic Chemistry 9 (October 10, 2013): 2048–78. http://dx.doi.org/10.3762/bjoc.9.243.

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This review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton. This motif is found in its intact or modified form in indolocarbazoles, macrocyclic polyketides (cytochalasan alkaloids), the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloids. Concerning their biological activity, molecular structure and synthesis, we have limited this review to the most inspiring examples. Within different congeners, we have selected a few members and discussed the synthetic routes in more detail. The putative biosynthetic pathways of the presented isoindole alkaloids are described as well.

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8

Yokoshima, Satoshi. "Synthesis of Polycyclic Natural Products through Skeletal Rearrangement." Synlett 31, no. 20 (July 23, 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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9

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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10

Thorat, Sagar S., and Ravindar Kontham. "Recent advances in the synthesis of oxaspirolactones and their application in the total synthesis of related natural products." Organic & Biomolecular Chemistry 17, no. 31 (2019): 7270–92. http://dx.doi.org/10.1039/c9ob01212e.

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Oxaspirolactones are ubiquitous structural motifs found in natural products and synthetic molecules with a diverse biochemical and physicochemical profile, and represent a valuable target in natural product chemistry and medicinal chemistry.

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11

Heasley, Brian. "Synthesis of Limonoid Natural Products." European Journal of Organic Chemistry 2011, no. 1 (October 18, 2010): 19–46. http://dx.doi.org/10.1002/ejoc.201001218.

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12

Morcillo, Sara P., Delia Miguel, Araceli G. Campaña, Luis Álvarez de Cienfuegos, José Justicia, and Juan M. Cuerva. "Recent applications of Cp2TiCl in natural product synthesis." Org. Chem. Front. 1, no. 1 (2014): 15–33. http://dx.doi.org/10.1039/c3qo00024a.

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13

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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14

Fang, Xianhe, and Xiangdong Hu. "Advances in the Synthesis of Lignan Natural Products." Molecules 23, no. 12 (December 19, 2018): 3385. http://dx.doi.org/10.3390/molecules23123385.

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Lignans comprise a family of secondary metabolites existing widely in plants and also in human food sources. As important components, these compounds play remarkable roles in plants' ecological functions as protection against herbivores and microorganisms. Meanwhile, foods rich in lignans have revealed potential to decrease of risk of cancers. To date, a number of promising bioactivities have been found for lignan natural products and their unnatural analogues, including antibacterial, antiviral, antitumor, antiplatelet, phosphodiesterase inhibition, 5-lipoxygenase inhibition, HIV reverse transcription inhibition, cytotoxic activities, antioxidant activities, immunosuppressive activities and antiasthmatic activities. Therefore, the synthesis of this family and also their analogues have attracted widespread interest from the synthetic organic chemistry community. Herein, we outline advances in the synthesis of lignan natural products in the last decade.

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15

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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16

Majhi, Sasadhar. "The Art of Total Synthesis of Bioactive Natural Products via Microwaves." Current Organic Chemistry 25, no. 9 (May 25, 2021): 1047–69. http://dx.doi.org/10.2174/1385272825666210303112302.

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Natural products are the most effective source of potential drug leads. The total synthesis of bioactive natural products plays a crucial role in confirming the hypothetical complex structure of natural products in the laboratory. The total synthesis of rare bioactive natural products is one of the great challenges for the organic synthetic community due to their complex structures, biochemical specificity, and difficult stereochemistry. Subsequently, the total synthesis is a long process in several cases, and it requires a substantial amount of time. Microwave irradiation has emerged as a greener tool in organic methodologies to reduce reaction time from days and hours to minutes and seconds. Moreover, this non-classical methodology increases product yields and purities, improves reproducibility, modifications of selectivity, simplification of work-up methods, and reduces unwanted side reactions. Such beneficial qualities have stimulated this review to cover the application of microwave irradiation in the field of the total synthesis of bioactive natural products for the first time during the last decade. An overview of the use of microwave irradiation, natural sources, structures, and biological activities of secondary metabolites is presented elegantly, focusing on the involvement of at least one or more steps by microwave irradiation as a green technique.

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17

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 (April 24, 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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18

Bai, Wen-Ju, Chen Lu, and Xiqing Wang. "Recent Advances in the Total Synthesis of Tetramic Acid-Containing Natural Products." Journal of Chemistry 2016 (2016): 1–13. http://dx.doi.org/10.1155/2016/8510278.

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With incredible bioactivities and fascinating structural complexities, tetramic acid- (TA-) containing natural products have attracted favorable attention among the organic chemistry community. Although the construction of the TA core is usually straightforward, the intricate C3-side chain sometimes asks for some deliberative strategy so as to fulfill an elegant total synthesis. This review mainly covers some exceptional synthetic examples for each type of natural product in recent years, showcasing the great achievements as well as unsettled obstacles in this area, in the hope of accelerating the synthetic and biological investigations for this unique type of natural product.

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19

Mori, Kenji. "Enantioselective Synthesis in Natural Products Chemistry. A Personal Account." Journal of Synthetic Organic Chemistry, Japan 53, no. 11 (1995): 952–62. http://dx.doi.org/10.5059/yukigoseikyokaishi.53.952.

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20

Adrian, Juliane, Leona J. Gross, and Christian B. W. Stark. "The direct oxidative diene cyclization and related reactions in natural product synthesis." Beilstein Journal of Organic Chemistry 12 (September 30, 2016): 2104–23. http://dx.doi.org/10.3762/bjoc.12.200.

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The direct oxidative cyclization of 1,5-dienes is a valuable synthetic method for the (dia)stereoselective preparation of substituted tetrahydrofurans. Closely related reactions start from 5,6-dihydroxy or 5-hydroxyalkenes to generate similar products in a mechanistically analogous manner. After a brief overview on the history of this group of transformations and a survey on mechanistic and stereochemical aspects, this review article provides a summary on applications in natural product synthesis. Moreover, current limitations and future directions in this area of chemistry are discussed.

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21

Donner, Christopher, Melvyn Gill, and Leonie Tewierik. "Synthesis of Pyran and Pyranone Natural Products." Molecules 9, no. 6 (May 31, 2004): 498–512. http://dx.doi.org/10.3390/90600498.

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22

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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23

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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24

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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25

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

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26

Zheng, Kuan, and Ran Hong. "Stereoconfining macrocyclizations in the total synthesis of natural products." Natural Product Reports 36, no. 11 (2019): 1546–75. http://dx.doi.org/10.1039/c8np00094h.

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27

Galanie, Stephanie, David Entwistle, and James Lalonde. "Engineering biosynthetic enzymes for industrial natural product synthesis." Natural Product Reports 37, no. 8 (2020): 1122–43. http://dx.doi.org/10.1039/c9np00071b.

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This review describes examples of the broadening industrial relevance of engineered secondary metabolism enzymes, natural products and analogs being made with these enzymes, and technology improvements that have enabled their development since 1999.

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28

Zhang, Hongbin. "Syntheses of Bioactive Natural Products and Natural-Product-Like Compounds Based on Their Key Structural Units." Synlett 25, no. 14 (June 3, 2014): 1953–70. http://dx.doi.org/10.1055/s-0033-1338641.

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29

Nájera, Carmen, Francisco Foubelo, José M. Sansano, and Miguel Yus. "Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds." Organic & Biomolecular Chemistry 18, no. 7 (2020): 1279–336. http://dx.doi.org/10.1039/c9ob02597a.

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30

Li, Jinshan, Kai Gao, Ming Bian, and Hanfeng Ding. "Recent advances in the total synthesis of cyclobutane-containing natural products." Organic Chemistry Frontiers 7, no. 1 (2020): 136–54. http://dx.doi.org/10.1039/c9qo01178a.

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31

Lindel, Thomas, and Fabia Hentschel. "Synthesis of Oximinotyrosine-Derived Marine Natural Products." Synthesis 2010, no. 02 (December 16, 2009): 181–204. http://dx.doi.org/10.1055/s-0029-1218615.

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32

Kinfe, Henok H. "Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis." Organic & Biomolecular Chemistry 17, no. 17 (2019): 4153–82. http://dx.doi.org/10.1039/c9ob00343f.

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33

Wu, Zhi-Chen, and Dale L. Boger. "The quest for supernatural products: the impact of total synthesis in complex natural products medicinal chemistry." Natural Product Reports 37, no. 11 (2020): 1511–31. http://dx.doi.org/10.1039/d0np00060d.

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This review summarizes and highlights recent advances in medicinal chemistry of natural products enabled by total synthesis that provide “supernatural products” with improved properties superseding the natural products themselves.

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Hanif, Novriyandi, Anggia Murni, Chiaki Tanaka, and Junichi Tanaka. "Marine Natural Products from Indonesian Waters." Marine Drugs 17, no. 6 (June 19, 2019): 364. http://dx.doi.org/10.3390/md17060364.

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Natural products are primal and have been a driver in the evolution of organic chemistry and ultimately in science. The chemical structures obtained from marine organisms are diverse, reflecting biodiversity of genes, species and ecosystems. Biodiversity is an extraordinary feature of life and provides benefits to humanity while promoting the importance of environment conservation. This review covers the literature on marine natural products (MNPs) discovered in Indonesian waters published from January 1970 to December 2017, and includes 732 original MNPs, 4 structures isolated for the first time but known to be synthetic entities, 34 structural revisions, 9 artifacts, and 4 proposed MNPs. Indonesian MNPs were found in 270 papers from 94 species, 106 genera, 64 families, 32 orders, 14 classes, 10 phyla, and 5 kingdoms. The emphasis is placed on the structures of organic molecules (original and revised), relevant biological activities, structure elucidation, chemical ecology aspects, biosynthesis, and bioorganic studies. Through the synthesis of past and future data, huge and partly undescribed biodiversity of marine tropical invertebrates and their importance for crucial societal benefits should greatly be appreciated.

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Ziarani, Ghodsi Mohammadi, Fatemeh Mohajer, and Zohreh kheilkordi. "Recent Progress Towards Synthesis of the Indolizidine Alkaloid 195B." Current Organic Synthesis 17, no. 2 (May 8, 2020): 82–90. http://dx.doi.org/10.2174/1570179417666200124104010.

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Background: Natural products have been received attention due to their importance in human life as those are biologically active. In this review, there are some reports through different methods related to the synthesis of the indolizidine 195B which was extracted from poisonous frog; however, due to respect nature, the synthesis of natural compounds such as indolizidine has been attracted much attention among scientists and researchers. Objective: This review discloses the procedures and methods to provide indolizidine 195B from 1989 to 2018 due to their importance as a natural product. Conclusion: There are several methods to give rise to the indolizidine 195B as a natural product that is highly active from the biological perspective in pharmaceutical chemistry. In summary, many protocols for the preparations of indolizidine 195B from various substrates, several reagents, and conditions have been reported from different aromatic and aliphatic.

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Opatz, Till, Leander Geske, and Eisuke Sato. "Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products." Synthesis 52, no. 19 (June 22, 2020): 2781–94. http://dx.doi.org/10.1055/s-0040-1707154.

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Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

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Brimble, Margaret, and Daniel Furkert. "Chemistry of Bis-Spiroacetal Systems: Natural Products, Synthesis and Stereochemistry." Current Organic Chemistry 7, no. 14 (September 1, 2003): 1461–84. http://dx.doi.org/10.2174/1385272033486404.

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38

Zhang, Zhipeng, Ying-jun Zhou, and Xiao-Wei Liang. "Total synthesis of natural products using photocycloaddition reactions of arenes." Organic & Biomolecular Chemistry 18, no. 29 (2020): 5558–66. http://dx.doi.org/10.1039/d0ob01204a.

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The photocycloaddition reaction of benzene with alkenes has become a significant approach for organic chemists and thus has been frequently utilized as a key step in the total synthesis of natural products.

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Ramachandran, P. Veeraraghavan, M. Venkat Ram Reddy, and Herbert C. Brown. "Tandem allylboration-ring-closing metathesis reactions for the preparation of biologically active molecules." Pure and Applied Chemistry 75, no. 9 (January 1, 2003): 1263–75. http://dx.doi.org/10.1351/pac200375091263.

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The development of asymmetric synthesis during the past two decades aided organic chemists considerably in the synthesis of complex natural products. Organoborane chemistry continues to play an important role in asymmetric synthesis. One of the important reactions that has become very common in the arsenal of synthetic chemists is allylboration and related reactions. Another important reaction that has recently attained enormous importance in organic chemistry is the ring-closing metathesis (RCM) reaction. Indeed, a combination of allylboration and RCM reactions provides an excellent route to cyclic ethers, lactones, lactams, etc. Herein, we describe a sequential asymmetric allylboration and RCM reaction protocol that has been utilized for the synthesis of several alpha-pyrone-containing natural products,particularly biologically active molecules.

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Eggert, Alina, Christoph Etling, Dennis Lübken, Marius Saxarra, and Markus Kalesse. "Contiguous Quaternary Carbons: A Selection of Total Syntheses." Molecules 25, no. 17 (August 24, 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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Ortiz, Aurelio, Miriam Castro, and Estibaliz Sansinenea. "3,4-Dihydroisocoumarins, Interesting Natural Products: Isolation, Organic Syntheses and Biological Activities." Current Organic Synthesis 16, no. 1 (February 4, 2019): 112–29. http://dx.doi.org/10.2174/1570179415666180924123439.

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Abstract:

Background:3,4-dihydroisocoumarins are an important small group belonging to the class of naturally occurring lactones isolated from different bacterial strains, molds, lichens, and plants. The structures of these natural compounds show various types of substitution in their basic skeleton and this variability influences deeply their biological activities. These lactones are structural subunits of several natural products and serve as useful intermediates in the synthesis of different heterocyclic molecules, which exhibit a wide range of biological activities, such as anti-inflammatory, antiplasmodial, antifungal, antimicrobial, antiangiogenic and antitumoral activities, among others. Their syntheses have attracted attention of many researchers reporting many synthetic strategies to achieve 3,4-dihydroisocoumarins and other related structures. </P><P> Objective: In this context, the isolation of these natural compounds from different sources, their syntheses and biological activities are reviewed, adding the most recent advances and related developments.Conclusion:This review aims to encourage further work on the isolation and synthesis of this class of natural products. It would be beneficial for synthetic as well as the medicinal chemists to design selective, optimized dihydroisocoumarin derivatives as potential drug candidates, since dihydroisocoumarin scaffolds have significant utility in the development of therapeutically relevant and biologically active compounds.

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McCulloch, M., and R. Barrow. "Towards a Synthesis of Naphthalene Derived Natural Products." Molecules 10, no. 10 (October 31, 2005): 1272–78. http://dx.doi.org/10.3390/10101272.

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KOSUGI, Hiroshi. "Asymmetric synthesis of natural products using chiral sulfoxides." Journal of Synthetic Organic Chemistry, Japan 45, no. 5 (1987): 472–80. http://dx.doi.org/10.5059/yukigoseikyokaishi.45.472.

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SATO, Kikumasa, and Seiichi INOUE. "Stereoselective synthesis of natural products of biological importance." Journal of Synthetic Organic Chemistry, Japan 46, no. 4 (1988): 318–33. http://dx.doi.org/10.5059/yukigoseikyokaishi.46.318.

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NAKAGAWA, Masako, Jinjun Liu, and Tohru HIND. "Total synthesis of antivirals marine natural products, eudistomins." Journal of Synthetic Organic Chemistry, Japan 48, no. 10 (1990): 891–906. http://dx.doi.org/10.5059/yukigoseikyokaishi.48.891.

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TSUBUKI, Masayoshi. "Natural Products Synthesis Utilizing Furan Derivatives as Synthons." Journal of Synthetic Organic Chemistry, Japan 51, no. 5 (1993): 399–411. http://dx.doi.org/10.5059/yukigoseikyokaishi.51.399.

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Zhang, Juan, Hua Zhang, Luis Alexandre Muehlmann, Cheng-Shi Jiang, and Yue-Wei Guo. "Synthesis and Structural Modification of Marine Natural Products." Molecules 22, no. 6 (May 26, 2017): 882. http://dx.doi.org/10.3390/molecules22060882.

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Martin, Stephen F. "Strategies for the synthesis of heterocyclic natural products." Journal of Heterocyclic Chemistry 31, no. 3 (May 1994): 679–86. http://dx.doi.org/10.1002/jhet.5570310308.

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Coleman, Robert S., Srinivas Reddy Gurrala, Soumya Mitra, and Amresh Raao. "Asymmetric Total Synthesis of Dibenzocyclooctadiene Lignan Natural Products." Journal of Organic Chemistry 70, no. 22 (October 2005): 8932–41. http://dx.doi.org/10.1021/jo051525i.

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Donate, Paulo Marcos, Rosangela da Silva, Gil Valdo José da Silva, and Carlos Alemán. "SYNTHESIS OF BENZOFURANOFURAN DERIVATIVES: MODEL OF NATURAL PRODUCTS." Synthetic Communications 31, no. 1 (January 2001): 151–54. http://dx.doi.org/10.1081/scc-100000191.

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