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Recent Advances in the Field of Natural Product Synthesis: A Themed Issue in Honor of Professor Ari Mauri Petri Koskinen’s Retirement

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

Deadline for manuscript submissions: 30 September 2024 | Viewed by 3160

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Special Issue Editors

Prof. Dr. Bruno Botta

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Guest Editor

Department of Chemistry and Technology of Drugs, Sapienza - University of Rome, Rome, Italy
Interests: secondary metabolites; natural products chemistry; natural products as anticancer agents; antibiotic resistance modulation by natural products; targeted therapy; molecular recognition; industrial hemp (Cannabis sativa L.)
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Trond Vidar Hansen

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Guest Editor

Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, POB 1068, N-0316 Oslo, Norway
Interests: pharmaceutical chemistry; synthetic organic chemistry; natural product synthesis; lipid chemistry; regulators of PPAR

Special Issue Information

Dear Colleagues,

Nature has been an invaluable source of medicines and traditional remedies since ancient times, which are mostly represented by herbs, animal products, and inorganic materials. Thanks to its biodiversity not only between animal and plant kingdoms but also among the various species, nature represents the largest library of compounds that has ever existed. In particular, medicinal plants represent a rich source of structurally diverse secondary metabolites, which can be exploited in the development of new clinically important compounds. Natural products feature enormous structural and chemical diversity that cannot be matched by any synthetic screening libraries and continue to remain the single most productive source of leads in modern drug discovery. The advent of new techniques in the separation, purification and characterization of novel compounds significantly improved the efficiency of these processes and, today, an important challenge is the generation of high-quality libraries of natural products that might allow the fast identification of lead compounds for drug discovery progression. In addition, the advent of powerful and user-friendly informatics tools for chemistry and biology further promoted the revolution of natural product screening in drug discovery. In the field of natural products research, organic chemistry has played a pivotal role, and the development of efficient, high-yielding, versatile, and innovative synthetic approaches allowed the production of natural products in quantities that otherwise would be inaccessible from natural sources, enabling more thorough biological evaluation. Indeed, accessing new chemical entities while retaining the biological relevance of natural chemotypes is a fundamental goal in the design of novel bioactive compound libraries. The general concept behind this Special Issue is to describe the recent advances in the field of natural product synthesis. In particular, it will gather the latest research trends in challenging organic synthesis of natural products, focusing on enantioselective synthesis, total synthesis, semisynthesis, biotransformation, and application of organic methodologies to total synthesis.

Prof. Dr. Bruno Botta
Prof. Dr. Trond Vidar Hansen
Guest Editors

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

natural products
synthesis
organocatalysis
enantiosynthesis
biotransformation
semisynthesis

Published Papers (4 papers)

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Research

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8 pages, 1787 KiB

Open AccessArticle

Synthesis of a Non-Symmetrical Disorazole C₁-Analogue and Its Biological Activity

by Luca Lizzadro, Oliver Spieß, Silke Reinecke, Marc Stadler and Dieter Schinzer

Molecules 2024, 29(5), 1123; https://doi.org/10.3390/molecules29051123 - 01 Mar 2024

Cited by 1 | Viewed by 626

Abstract

The synthesis of a novel disorazole C₁ analogue is described, and its biological activity as a cytotoxic compound is reported. Based on our convergent and flexible route to the disorazole core, we wish to report a robust strategy to synthesize a non-symmetrical disorazole in which we couple one half of the molecule containing the naturally occurring oxazole heterocycle and the second half of the disorazole macrocycle containing a thiazole heterocycle. This resulted in a very unusual non-symmetrical disorazole C₁ analogue containing two different heterocycles, and its biological activity was studied. This provided exciting information about SAR (structure-activity-relationship) for this highly potent class of antitumor compounds. Full article

(This article belongs to the Special Issue Recent Advances in the Field of Natural Product Synthesis: A Themed Issue in Honor of Professor Ari Mauri Petri Koskinen’s Retirement)

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15 pages, 4839 KiB

Open AccessArticle

Biological Evaluations, NMR Analyses, Molecular Modeling Studies, and Overview of the Synthesis of the Marine Natural Product (−)-Mucosin

by Jens M. J. Nolsøe, Jarl Underhaug, Åshild Moi Sørskar, Simen Gjelseth Antonsen, Karl E. Malterud, Osman Gani, Qiong Fan, Marit Hjorth, Thomas Sæther, Trond V. Hansen and Yngve H. Stenstrøm

Molecules 2024, 29(5), 994; https://doi.org/10.3390/molecules29050994 - 24 Feb 2024

Viewed by 842

Abstract

Natural products obtained from marine organisms continue to be a rich source of novel structural architecture and of importance in drug discovery, medicine, and health. However, the success of such endeavors depends on the exact structural elucidation and access to sufficient material, often by stereoselective total synthesis, of the isolated natural product of interest. (−)-Mucosin (1), a fatty acid derivative, previously presumed to contain a rare cis-bicyclo[4.3.0]non-3-ene moiety, has since been shown to be the trans-congener. Analytically, the fused bicyclic ring system in (−)-1 constitutes a particular challenge in order to establish its relative and absolute stereochemistry. Herein, data from biological evaluations, NMR and molecular modeling studies of (−)-1 are presented. An overview of the synthetic strategies enabling the exact structural elucidation of (−)-mucosin (1) is also presented. Full article

(This article belongs to the Special Issue Recent Advances in the Field of Natural Product Synthesis: A Themed Issue in Honor of Professor Ari Mauri Petri Koskinen’s Retirement)

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15 pages, 1374 KiB

Open AccessArticle

Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of Polyunsaturated C18:3 Omega-3 and Omega-6 MEL Triene Derivatives

by Svanur Sigurjónsson and Gudmundur G. Haraldsson

Molecules 2024, 29(1), 223; https://doi.org/10.3390/molecules29010223 - 31 Dec 2023

Viewed by 695

Abstract

The asymmetric synthesis of polyunsaturated triene C18:3 n-3 and C18:3 n-6 methoxylated ether lipids (MEL) of the 1-O-alkyl-sn-glycerol type is described as possible structural candidates for a triene C18:3 MEL of an unknown identity found in a mixture of shark and dogfish liver oil. Their C18:3 hydrocarbon chains constitute an all-cis methylene skipped n-3 or n-6 triene framework, along with a methoxyl group at the 2′-position and R-configuration of the resulting stereogenic center. The methoxylated polyenes are attached by an ether linkage to the pro-S hydroxymethyl group of the glycerol backbone. The syntheses were based on the polyacetylene approach that involves a semi-hydrogenation of the resulting triynes. Both syntheses were started from our previously described enantio- and diastereomerically pure isopropylidene-protected glyceryl glycidyl ether, a double-C3 building block that was designed as a head group synthon for the synthesis of various types of MELs. Full article

(This article belongs to the Special Issue Recent Advances in the Field of Natural Product Synthesis: A Themed Issue in Honor of Professor Ari Mauri Petri Koskinen’s Retirement)

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Review

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20 pages, 3620 KiB

Open AccessReview

Recent Advances in the Total Synthesis of Spirotryprostatin Alkaloids

by Jing Hu, Zhen-Xi Niu and Jun-Feng Wang

Molecules 2024, 29(7), 1655; https://doi.org/10.3390/molecules29071655 - 07 Apr 2024

Viewed by 443

Abstract

Spirotryprostatin alkaloids, a class of alkaloids with a unique spirocyclic indoledionepiperazine structure, were first extracted from the fermentation broth of Aspergillus fumigatus and have garnered significant attention in the fields of biology and pharmacology. The investigation into the pharmacological potential of this class of alkaloids has unveiled promising applications in drug discovery and development. Notably, certain spirotryprostatin alkaloids have demonstrated remarkable anti-cancer activity, positioning them as potential candidates for anti-tumor drug development. In recent years, organic synthetic chemists have dedicated efforts to devise efficient and viable strategies for the total synthesis of spirotryprostatin alkaloids, aiming to meet the demands within the pharmaceutical domain. The construction of the spiro-C atom within the spirotryprostatin scaffold and the chirality control at the spiro atomic center emerge as pivotal aspects in the synthesis of these compounds. This review categorically delineates the synthesis of spirotryprostatin alkaloids based on the formation mechanism of the spiro-C atom. Full article

(This article belongs to the Special Issue Recent Advances in the Field of Natural Product Synthesis: A Themed Issue in Honor of Professor Ari Mauri Petri Koskinen’s Retirement)

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