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Recent Advances in Organic Synthesis Related to Natural Compounds
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Recent Advances in Organic Synthesis Related to Natural Compounds

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 31 December 2024 | Viewed by 12978

Special Issue Editor

Dr. Faïza Diaba

E-Mail Website
Guest Editor
Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, 08028 Barcelona, Spain
Interests: photoredox catalysis; radical cyclizations; natural compounds; alkaloids; nitrogen heterocycles; green chemistry

Special Issue Information

Dear Colleagues,

Synthesis of natural compounds is one of the most challenging and exciting areas of organic synthesis that has consistently remained relevant. Since the preparation of urea by Friedrich Wöhler from ammonium cyanate in 1828, natural product synthesis, both total and partial, has become an important field of investigation recognized by the Nobel Prize in Chemistry several times during the last century. Moreover, natural products are continually explored in the development of new bioactive compounds with industrial applications.

For this Special Issue, we invite researchers to submit original research articles that describe their most recent advances in the total or partial synthesis (semi-synthesis) of simple or complex natural compounds. In addition, synthetic approaches toward bioactive molecules inspired in existing natural compounds are also required. In this Special Issue we are placing particular emphasis on processes involving radical species, including photocatalyzed reactions, organo- and transition-metal-catalyzed transformations, combinatorial chemistry, and formation of C-C bonds through C-H activation. Short review articles related to specific reactions involved in the synthesis of natural compounds or the different strategies involved in the synthesis of advanced intermediates are also welcomed.

Dr. Faïza Diaba
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. Molecules is an international peer-reviewed open access semimonthly 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 2700 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

  • total synthesis
  • natural compounds
  • semi-synthesis
  • alkaloids
  • carbocycles
  • scaffolds

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Published Papers (8 papers)

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Research

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19 pages, 5662 KiB  
Article
Design, Synthesis, Structural Insights, Tyrosinase Inhibition, and Sun Protection Factor of New Thiosemicarbazone Derivatives
by Sebastiano Masuri, Benedetta Era, Francesca Pintus, Sonia Floris, Francesca Meloni, Francesca Pettinau, Enrico Podda, Maria Grazia Cabiddu, Antonella Fais and Tiziana Pivetta
Molecules 2024, 29(23), 5629; https://doi.org/10.3390/molecules29235629 - 28 Nov 2024
Viewed by 197
Abstract
Tyrosinase, a key protein in the biosynthesis of melanin pigments, is crucial in determining skin pigmentation. Inhibiting tyrosinase activity is a promising approach for treating conditions related to excessive pigmentation. For the synthesis of more potent tyrosinase inhibitors, we combined two approaches, para-substitution [...] Read more.
Tyrosinase, a key protein in the biosynthesis of melanin pigments, is crucial in determining skin pigmentation. Inhibiting tyrosinase activity is a promising approach for treating conditions related to excessive pigmentation. For the synthesis of more potent tyrosinase inhibitors, we combined two approaches, para-substitution and lipophilicity, to enhance the inhibitory properties of (E)-2-(4-hydroxybenzylidene)hydrazine-1-carbotiamide, whose enzyme inhibitory properties have been previously demonstrated. The newly synthesized compounds showed potent inhibition activity against tyrosinase in the micromolar concentration range. The synthesised compounds were up to 41 times more effective than kojic acid. In addition to this biological activity, all molecules were evaluated for their sun protection factor to determine their photoprotective effects. All the compounds showed higher efficacy than reference compounds, used as sunscreens in photoprotective preparations. All compounds were noncytotoxic at the concentration required to inhibit tyrosinase activity. With the aim of defining the potential binding modes and the kind of interactions between the studied molecules and the catalytic site of mushroom tyrosinase, molecular docking simulations were also performed. Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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19 pages, 5916 KiB  
Article
A Ligand-Free Approach towards Coumarin Analogs via Natural Deep Eutectic Solvent-Mediated Suzuki–Miyaura Coupling
by Annita Katopodi, Nikolaos Nikolaou, Vasiliki Kakokefalou, Eleni Alexandratou, Manolis Matzapetakis, Maria Zervou and Anastasia Detsi
Molecules 2024, 29(18), 4398; https://doi.org/10.3390/molecules29184398 - 16 Sep 2024
Cited by 1 | Viewed by 804
Abstract
A ligand-free approach for the Suzuki-Miyaura cross coupling reaction using Natural Deep Eutectic Solvents (NaDES) towards coumarin analogs is described. A model reaction between the synthetically prepared 3-(4-acetyloxy-phenyl)-6-bromo-4-methyl-coumarin (3b) and phenylboronic acid was performed in five different NaDES as well as [...] Read more.
A ligand-free approach for the Suzuki-Miyaura cross coupling reaction using Natural Deep Eutectic Solvents (NaDES) towards coumarin analogs is described. A model reaction between the synthetically prepared 3-(4-acetyloxy-phenyl)-6-bromo-4-methyl-coumarin (3b) and phenylboronic acid was performed in five different NaDES as well as in pure glycerol, using two inorganic bases and palladium catalysts. The reaction proceeded smoothly in Choline Chloride/Glycerol (ChCl/Gly) and Betaine/Glycerol (Bet/Gly) NaDES at 90 °C in 24 h, affording the desired product in high yields up to 95%. The combination of K2CO3, Pd(OAc)2 and ChCl/Gly NaDES provided optimum yields and high purity of the desired compounds, while the solvent was successfully recycled and reused up to two times. The developed methodology is applicable to boronic acids bearing various substituents. The formation of palladium nanoparticles in the reaction mixture was observed, and the size of the nanoparticles was associated with the reaction yield. In addition, in all the glycerol-based NaDES, an effective removal of the acetyl group of the acetyloxy–coumarin analogs was observed; thus, it is noteworthy that the Suzuki–Miyaura coupling and the deacetylation reaction were achieved in one pot. The ten novel coumarin derivatives synthesized were structurally characterized using 1D and 2D NMR spectroscopy and were tested for their cytotoxicity against the A431 squamous cancer cell line, presenting significant activity. Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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20 pages, 3311 KiB  
Article
Microwave-Assisted Atom Transfer Radical Cyclization in the Synthesis of 3,3-Dichloro-γ- and δ-Lactams from N-Alkenyl-Tethered Trichloroacetamides Catalyzed by RuCl2(PPh3)3 and Their Cytotoxic Evaluation
by Faïza Diaba, Alexandra G. Sandor and María del Carmen Morán
Molecules 2024, 29(9), 2035; https://doi.org/10.3390/molecules29092035 - 28 Apr 2024
Viewed by 882
Abstract
An expeditious synthesis of γ- and δ-lactams from tethered alkenyl trichloroacetamides in the presence of 5% of RuCl2(PPh3)3 is reported. In this investigation we have demonstrated that microwave activation significantly enhances reaction rates, leading to the formation of [...] Read more.
An expeditious synthesis of γ- and δ-lactams from tethered alkenyl trichloroacetamides in the presence of 5% of RuCl2(PPh3)3 is reported. In this investigation we have demonstrated that microwave activation significantly enhances reaction rates, leading to the formation of the corresponding lactams in yields ranging from good to excellent. Thus, we have been able to prepare a wide range of lactams, including indole and morphan bicyclic scaffolds, where the corresponding reactions were completely diastereoselective. This process was successfully extended to α,α-dichloroamides without affecting either their yield or their diastereoselectivity. Some of the lactams prepared in this work were evaluated for their hemolytic and cytotoxic responses. All compounds were found to be non-hemolytic at the tested concentration, indicating their safety profile in terms of blood cell integrity. Meanwhile, they exhibited interesting cytotoxicity responses that depend on both their lactam structure and cell line. Among the molecules tested, γ-lactam 2a exhibited the lowest IC50 values (100–250 µg/mL) as a function of its cell line, with promising selectivity against squamous carcinoma cells (A431) in comparison with fibroblasts (3T3 cell line). Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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15 pages, 989 KiB  
Article
Bridged 1,2,4-Trioxolanes: SnCl4—Catalyzed Synthesis and an In Vitro Study against S. mansoni
by Peter S. Radulov, Ivan A. Yaremenko, Jennifer Keiser and Alexander O. Terent’ev
Molecules 2023, 28(13), 4913; https://doi.org/10.3390/molecules28134913 - 22 Jun 2023
Cited by 3 | Viewed by 1341
Abstract
A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl4 was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl4 as a catalyst and varying the solvent. [...] Read more.
A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl4 was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl4 as a catalyst and varying the solvent. A wide range of bridged 1,2,4-trioxolanes (ozonides) was obtained in yields from 50 to 84%. The ozonide cycle was moderately resistant to the reduction of the ester group near the peroxide cycle to alcohol with LiAlH4. The bridged ozonides were evaluated for their antischistosomal activity. These ozonides exhibited a very high activity against newly transformed schistosomula and adult Schistosoma mansoni. Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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12 pages, 3031 KiB  
Article
Organocatalytic Asymmetric Peroxidation of γ,δ-Unsaturated β-Keto Esters—A Novel Route to Chiral Cycloperoxides
by Mary C. Hennessy, Hirenkumar Gandhi and Timothy P. O’Sullivan
Molecules 2023, 28(11), 4317; https://doi.org/10.3390/molecules28114317 - 24 May 2023
Cited by 2 | Viewed by 2111
Abstract
A methodology for the asymmetric peroxidation of γ,δ-unsaturated β-keto esters is presented. Using a cinchona-derived organocatalyst, the target δ-peroxy-β-keto esters were obtained in high enantiomeric ratios of up to 95:5. Additionally, these δ-peroxy esters can be readily reduced to chiral δ-hydroxy-β-keto esters without [...] Read more.
A methodology for the asymmetric peroxidation of γ,δ-unsaturated β-keto esters is presented. Using a cinchona-derived organocatalyst, the target δ-peroxy-β-keto esters were obtained in high enantiomeric ratios of up to 95:5. Additionally, these δ-peroxy esters can be readily reduced to chiral δ-hydroxy-β-keto esters without impacting the β-keto ester functionality. Importantly, this chemistry opens up a concise route to chiral 1,2-dioxolanes, a common motif in many bioactive natural products, via a novel P2O5-mediated cyclisation of the corresponding δ-peroxy-β-hydroxy esters. Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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16 pages, 11400 KiB  
Article
Fungal Secondary Metabolites/Dicationic Pyridinium Iodide Combinations in Combat against Multi-Drug Resistant Microorganisms
by Ayoub M. Abdelalatif, Bassma H. Elwakil, Mohamed Zakaria Mohamed, Mohamed Hagar and Zakia A. Olama
Molecules 2023, 28(6), 2434; https://doi.org/10.3390/molecules28062434 - 7 Mar 2023
Cited by 11 | Viewed by 2058
Abstract
The spread of antibiotic-resistant opportunistic microbes is a huge socioeconomic burden and a growing concern for global public health. In the current study, two endophytic fungal strains were isolated from Mangifera Indica roots and identified as Aspergillus niger MT597434.1 and Trichoderma lixii KU324798.1. [...] Read more.
The spread of antibiotic-resistant opportunistic microbes is a huge socioeconomic burden and a growing concern for global public health. In the current study, two endophytic fungal strains were isolated from Mangifera Indica roots and identified as Aspergillus niger MT597434.1 and Trichoderma lixii KU324798.1. Secondary metabolites produced by A. niger and T. lixii were extracted and tested for their antimicrobial activity. The highest activity was noticed against Staphylococcus aureus and E. coli treated with A. niger and T. lixii secondary metabolites, respectively. A. niger crude extract was mainly composed of Pentadecanoic acid, 14-methyl-, methyl ester and 9-Octadecenoic acid (Z)-, methyl ester (26.66 and 18.01%, respectively), while T. lixii crude extract’s major components were 2,4-Decadienal, (E,E) and 9-Octadecenoic acid (Z)-, and methyl ester (10.69 and 10.32%, respectively). Moreover, a comparative study between the fungal extracts and dicationic pyridinium iodide showed that the combination of A. niger and T. lixii secondary metabolites with dicationic pyridinium iodide compound showed a synergistic effect against Klebsiella pneumoniae. The combined formulae inhibited the bacterial growth after 4 to 6 h through cell wall breakage and cells deformation, with intracellular components leakage and increased ROS production. Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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15 pages, 1738 KiB  
Article
Fused Pyrroles in Cholestane and Norcholestane Side Chains: Acaricidal and Plant Growth-Promoting Effects
by María G. De los Santos, Marcos Cua-Basulto, Anallely Huepalcalco, Wendy Delit, Jesús Sandoval-Ramírez, Adolfo López-Torres, Esaú Ruiz-Sánchez and María A. Fernández-Herrera
Molecules 2022, 27(23), 8466; https://doi.org/10.3390/molecules27238466 - 2 Dec 2022
Cited by 3 | Viewed by 1815
Abstract
Herein, we describe the synthesis and characterization of fused pyrroles in cholestane and norcholestane side chains derived from kryptogenin and diosgenin, respectively. Both conventional and microwave heating techniques were used to synthesize the steroidal pyrroles from primary amines, with the microwave method producing [...] Read more.
Herein, we describe the synthesis and characterization of fused pyrroles in cholestane and norcholestane side chains derived from kryptogenin and diosgenin, respectively. Both conventional and microwave heating techniques were used to synthesize the steroidal pyrroles from primary amines, with the microwave method producing the highest yields. In particular, the norcholestane pyrroles were tested as acaricides against the two-spotted spider mite (Tetranychus urticae Koch) under laboratory conditions and as plant growth promoters on habanero pepper (Capsicum chinense Jacq) under greenhouse conditions. Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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Review

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23 pages, 4336 KiB  
Review
The Corey-Seebach Reagent in the 21st Century: A Review
by Muhammad Haroon, Ameer Fawad Zahoor, Sajjad Ahmad, Asim Mansha, Muhammad Irfan, Aqsa Mushtaq, Rabia Akhtar, Ali Irfan, Katarzyna Kotwica-Mojzych and Mariusz Mojzych
Molecules 2023, 28(11), 4367; https://doi.org/10.3390/molecules28114367 - 26 May 2023
Cited by 5 | Viewed by 2539
Abstract
The Corey-Seebach reagent plays an important role in organic synthesis because of its broad synthetic applications. The Corey-Seebach reagent is formed by the reaction of an aldehyde or a ketone with 1,3-propane-dithiol under acidic conditions, followed by deprotonation with n-butyllithium. A large [...] Read more.
The Corey-Seebach reagent plays an important role in organic synthesis because of its broad synthetic applications. The Corey-Seebach reagent is formed by the reaction of an aldehyde or a ketone with 1,3-propane-dithiol under acidic conditions, followed by deprotonation with n-butyllithium. A large variety of natural products (alkaloids, terpenoids, and polyketides) can be accessed successfully by utilizing this reagent. This review article focuses on the recent contributions (post-2006) of the Corey-Seebach reagent towards the total synthesis of natural products such as alkaloids (lycoplanine A, diterpenoid alkaloids, etc.), terpenoids (bisnorditerpene, totarol, etc.), polyketide (ambruticin J, biakamides, etc.), and heterocycles such as rodocaine and substituted pyridines, as well and their applications towards important organic synthesis. Full article
(This article belongs to the Special Issue Recent Advances in Organic Synthesis Related to Natural Compounds)
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