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Organics
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New Reactions and Strategies for Natural Product Synthesis
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New Reactions and Strategies for Natural Product Synthesis

A special issue of Organics (ISSN 2673-401X).

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 19526

Special Issue Editor

Dr. Takahiro Suzuki

E-Mail Website
Guest Editor
Department of Chemistry, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan
Interests: organic synthesis; total synthesis; cascade reaction; cycloaddition reaction; natural products; chemical biology

Special Issue Information

Dear Colleagues,

Since ancient eras, natural products have been used by mankind as medicines and poisons due to their various effects on living organisms. The development of synthetic organic chemistry after the 20th century has contributed to the promotion of human health through the synthesis of both natural products and their derivatives, which have been used as pharmaceuticals and agrochemicals. Nevertheless, it still remains difficult to synthesize natural products that have complex ring structures and dense functional groups. Since the synthesis of these compounds requires elaborate synthetic strategies and efficient cyclization reactions, it has become a very challenging task.

For efficient and short-step synthesis of complex natural products, synthetic studies using model compounds are often conducted. Even if the synthetic pathways do not reach natural products, significant discoveries in synthetic chemistry are often found in synthetic studies.

This Special Issue highlights new and important discoveries, especially in natural product synthesis. In particular, we invite short communications that include recent results on total synthesis-oriented reaction development, synthetic strategies, and mechanistic considerations in biosynthesis, as well as full papers that include comprehensive studies on natural product synthesis. Review articles by experts in the field are also welcome.

Dr. Takahiro Suzuki
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Organics is an international peer-reviewed open access quarterly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1000 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • organic synthesis
  • natural products
  • development of synthetic methodology
  • catalytic reaction
  • pericyclic reaction
  • organometallic reaction
  • chemo-, regio-, and stereoselectivity
  • radical reaction
  • electrochemical reaction
  • structure determination

Published Papers (6 papers)

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Research

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11 pages, 2347 KiB  
Article
Divergent Synthesis of Four Monomeric Ellagitannins toward the Total Synthesis of an Oligomeric Ellagitannin, Nobotanin K
by Hajime Hashimoto, Shinnosuke Wakamori, Kazutada Ikeuchi and Hidetoshi Yamada
Organics 2022, 3(3), 293-303; https://0-doi-org.brum.beds.ac.uk/10.3390/org3030022 - 06 Sep 2022
Cited by 2 | Viewed by 1552
Abstract
Oligomeric ellagitannins are challenging synthetic targets due to the need for an abundant supply of their composed monomeric ellagitannins and a synthetic methodology to connect them. This work focused on the divergent synthesis of the four monomeric ellagitannins from a common intermediate as [...] Read more.
Oligomeric ellagitannins are challenging synthetic targets due to the need for an abundant supply of their composed monomeric ellagitannins and a synthetic methodology to connect them. This work focused on the divergent synthesis of the four monomeric ellagitannins from a common intermediate as a step toward the total synthesis of nobotanin K, a class of compounds that includes oligomeric ellagitannins and were isolated in plants belonging to the Melastomataceae family. Implementing our method, the four natural products could be easily supplied, suggesting that through this novel route, the total synthesis of nobotanin K could be achieved smoothly. Full article
(This article belongs to the Special Issue New Reactions and Strategies for Natural Product Synthesis)
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9 pages, 1695 KiB  
Article
Enantioselective Total Synthesis of Multifidene, a Sex Pheromone of Brown Algae
by Taiki Umezawa, Misaki Hara, Nana Kinoshita-Terauchi and Fuyuhiko Matsuda
Organics 2022, 3(3), 187-195; https://0-doi-org.brum.beds.ac.uk/10.3390/org3030015 - 08 Jul 2022
Cited by 2 | Viewed by 1720
Abstract
The total synthesis of multifidene, a sex pheromone found in brown algae, is described. The synthesis features the highly enantioselective and diastereoselective addition reaction of an aldehyde to a nitroolefin in the presence of a Hayashi–Jørgensen catalyst and a Nef reaction initiated by [...] Read more.
The total synthesis of multifidene, a sex pheromone found in brown algae, is described. The synthesis features the highly enantioselective and diastereoselective addition reaction of an aldehyde to a nitroolefin in the presence of a Hayashi–Jørgensen catalyst and a Nef reaction initiated by visible light irradiation. These key reactions enabled the 11-step synthesis from commercially available compounds. The synthetic pheromones are examined with gametes. Full article
(This article belongs to the Special Issue New Reactions and Strategies for Natural Product Synthesis)
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11 pages, 6585 KiB  
Communication
1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles
by Tomas Opsomer, Kaat Valkeneers, Ana Ratković and Wim Dehaen
Organics 2021, 2(4), 404-414; https://0-doi-org.brum.beds.ac.uk/10.3390/org2040024 - 06 Dec 2021
Cited by 4 | Viewed by 3419
Abstract
1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles [...] Read more.
1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide. Full article
(This article belongs to the Special Issue New Reactions and Strategies for Natural Product Synthesis)
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7 pages, 1505 KiB  
Communication
Adamantane-Functionalized Phthalimide Scaffold: Pathways to Supramolecular Interactions and Drug Discovery
by Hamidou Keita
Organics 2021, 2(4), 388-394; https://0-doi-org.brum.beds.ac.uk/10.3390/org2040022 - 11 Nov 2021
Cited by 1 | Viewed by 3618
Abstract
Herein, the synthesis of a novel adamantanyl-functionalized phthalimide scaffold is demonstrated. The novel compound could be used as a precursor for various synthetic pathways owing to the generic use of adamantane substituents as the driving force for supramolecular interactions with macrocycles and N-substituted [...] Read more.
Herein, the synthesis of a novel adamantanyl-functionalized phthalimide scaffold is demonstrated. The novel compound could be used as a precursor for various synthetic pathways owing to the generic use of adamantane substituents as the driving force for supramolecular interactions with macrocycles and N-substituted phthalimide derivatives as a core structure in numerous drugs. The adamantanyl-functionalized phthalimide scaffold contains bromide groups on the C4 and C5 positions of the benzene ring, effectively allowing further facile modifications of the scaffold. The structure was fully characterized including single-crystal X-ray crystallography. The crystal structure shows an adamantane moiety at an angle of 115.57(7)° to the phthalimide core, hence sterically freeing the adamantane unit for host–guest interactions. Full article
(This article belongs to the Special Issue New Reactions and Strategies for Natural Product Synthesis)
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Review

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16 pages, 3078 KiB  
Review
Total Syntheses of Chloropupukeananin and Its Related Natural Products
by Takahiro Suzuki
Organics 2022, 3(3), 304-319; https://0-doi-org.brum.beds.ac.uk/10.3390/org3030023 - 09 Sep 2022
Cited by 1 | Viewed by 1722
Abstract
Chloropupukeananin is a natural product that inhibits HIV-1 replication and has antitumor activity. Its structure consists of a chlorinated tricyclo[4.3.1.03,7]decane core skeleton with an array of highly oxidized multifunctional groups. In the biosynthesis of chloropupukeananin, (+)-iso-A82775C and (−)-maldoxin are employed as [...] Read more.
Chloropupukeananin is a natural product that inhibits HIV-1 replication and has antitumor activity. Its structure consists of a chlorinated tricyclo[4.3.1.03,7]decane core skeleton with an array of highly oxidized multifunctional groups. In the biosynthesis of chloropupukeananin, (+)-iso-A82775C and (−)-maldoxin are employed as biosynthetic precursors for the intermolecular Diels–Alder and carbonyl–ene reactions, followed by the migration of the p-orcellinate group. Chloropupukeanolides and chloropestolides are intermediates and isomers in biosynthesis; their unique chemical structures and biosynthetic pathways have attracted significant attention from synthetic chemists. In this review, I present the synthetic studies on chloropupukeananin and its related compounds that have been conducted thus far. Full article
(This article belongs to the Special Issue New Reactions and Strategies for Natural Product Synthesis)
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21 pages, 7259 KiB  
Review
Recent Applications of Pd-Catalyzed Suzuki–Miyaura and Buchwald–Hartwig Couplings in Pharmaceutical Process Chemistry
by Balaram S. Takale, Fan-Yi Kong and Ruchita R. Thakore
Organics 2022, 3(1), 1-21; https://0-doi-org.brum.beds.ac.uk/10.3390/org3010001 - 18 Jan 2022
Cited by 15 | Viewed by 6548
Abstract
Cross-coupling reactions have changed the way complex molecules are synthesized. In particular, Suzuki–Miyaura and Buchwald–Hartwig amination reactions have given opportunities to elegantly make pharmaceutical ingredients. Indeed, these reactions are at the forefront of both the stages of drug development, medicinal chemistry, and process [...] Read more.
Cross-coupling reactions have changed the way complex molecules are synthesized. In particular, Suzuki–Miyaura and Buchwald–Hartwig amination reactions have given opportunities to elegantly make pharmaceutical ingredients. Indeed, these reactions are at the forefront of both the stages of drug development, medicinal chemistry, and process chemistry. On the one hand, these reactions have given medicinal chemists a resource to derivatize the core compound to arrive at scaffold rapidly. On the other hand, these cross couplings have offered the process chemists a smart tool to synthesize the development candidates safely, quickly, and efficiently. Generally, the application of cross-coupling reactions is broad. This review will specifically focus on their real (pharma) world applications in large-scale synthesis appearing in the last three years. Full article
(This article belongs to the Special Issue New Reactions and Strategies for Natural Product Synthesis)
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