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Total Synthesis of Natural Products
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Total Synthesis of Natural Products

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

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 23073

Special Issue Editors

Prof. Dr. Ari Koskinen

E-Mail Website
Guest Editor
Department of Chemistry and Materials Science, Aalto University School of Chemical Engineering, Kemistintie 1, P.O. Box 16100, 02150 Espoo, Finland
Interests: organic synthesis; asymmetric synthesis; natural products
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Magne Olav Sydnes

E-Mail Website
Guest Editor
Universitetet i Stavanger, Stavanger, Norway
Interests: natural product synthesis; medicinal chemistry; catalysis; chemical biology; analytical chemistry; environmental chemistry
Prof. Dr. Joanne Harvey

E-Mail Website
Guest Editor
Victoria University of Wellington, Wellington, New Zealand
Interests: natural product synthesis; nature-inspired drug discovery; design and synthesis of natural product analogues; reaction mechanism
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In the course of evolution, Nature has developed an inexhaustible diversity of biologically active natural products. The great diversity of natural products lends challenge to their synthesis, encouraging the development of new synthetic methodology. Total synthesis plays an important role as a means to achieve the unambiguous assignment of chemical structure and obtain sufficient material for biological assessment and consequent applications. In this forthcoming Special Issue of Molecules entitled “Total Synthesis of Natural Products”, we invite contributions on the total synthesis of natural products, including recent key findings, latest developments, and innovative synthetic approaches.

Original articles, as well as reviews, regarding recent advancements in natural product total synthesis are sought for inclusion in this Special Issue. As Guest Editors, we cordially invite researchers to submit their recent advances in the field to this Special Issue of Molecules.

Prof. Dr. Ari Koskinen
Prof. Dr. Magne O. Sydnes
Prof. Dr. Joanne Harvey
Guest Editors

Keywords

  • Natural products
  • Plant-derived natural products
  • Marine natural products 
  • Microbial natural products
  • Alkaloids
  • Heterocycles
  • Macrocycles
  • Peptides
  • Terpenoids
  • Polyketides
  • Total synthesis

Published Papers (6 papers)

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Research

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15 pages, 2025 KiB  
Article
Concise Large-Scale Synthesis of Tomatidine, A Potent Antibiotic Natural Product
by Chad Normandin and Pierre-Luc Boudreault
Molecules 2021, 26(19), 6008; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26196008 - 03 Oct 2021
Cited by 4 | Viewed by 3427
Abstract
Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high [...] Read more.
Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high cost, an efficient and scalable multi-gram synthesis of tomatidine has been developed. This synthesis uses a Suzuki–Miyaura-type coupling reaction as a key step to graft an enantiopure F-ring side chain to the steroidal scaffold of the natural product, which was accessible from low-cost and commercially available diosgenin. A Lewis acid-mediated spiroketal opening followed by an azide substitution and reduction sequence is employed to generate the spiroaminoketal motif of the natural product. Overall, this synthesis produced 5.2 g in a single pass in 15 total steps and 15.2% yield using a methodology that is atom economical, scalable, and requires no flash chromatography purifications. Full article
(This article belongs to the Special Issue Total Synthesis of Natural Products)
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10 pages, 1154 KiB  
Article
Organocatalytic Enantiospecific Total Synthesis of Butenolides
by Rudrakshula Madhavachary, Rosy Mallik and Dhevalapally B. Ramachary
Molecules 2021, 26(14), 4320; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26144320 - 16 Jul 2021
Cited by 10 | Viewed by 3801
Abstract
Biologically important, chiral natural products of butenolides, (−)-blastmycinolactol, (+)-blastmycinone, (−)-NFX-2, (+)-antimycinone, lipid metabolites, (+)-ancepsenolide, (+)-homoancepsenolide, mosquito larvicidal butenolide and their analogues were synthesized in very good yields in a sequential one-pot manner by using an organocatalytic reductive coupling and palladium-mediated reductive deoxygenation or [...] Read more.
Biologically important, chiral natural products of butenolides, (−)-blastmycinolactol, (+)-blastmycinone, (−)-NFX-2, (+)-antimycinone, lipid metabolites, (+)-ancepsenolide, (+)-homoancepsenolide, mosquito larvicidal butenolide and their analogues were synthesized in very good yields in a sequential one-pot manner by using an organocatalytic reductive coupling and palladium-mediated reductive deoxygenation or organocatalytic reductive coupling and silica-mediated reductive deamination as the key steps. Full article
(This article belongs to the Special Issue Total Synthesis of Natural Products)
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22 pages, 2497 KiB  
Article
Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioisomers for Antimalarial, Antiproliferative and Antimicrobial Activities
by Katja S. Håheim, Emil Lindbäck, Kah Ni Tan, Marte Albrigtsen, Ida T. Urdal Helgeland, Clémence Lauga, Théodora Matringe, Emily K. Kennedy, Jeanette H. Andersen, Vicky M. Avery and Magne O. Sydnes
Molecules 2021, 26(11), 3268; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113268 - 30 May 2021
Cited by 7 | Viewed by 2929
Abstract
A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. [...] Read more.
A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 µM; 9b: MBIC = 100 µM). Full article
(This article belongs to the Special Issue Total Synthesis of Natural Products)
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10 pages, 2571 KiB  
Article
Total Synthesis of Phorbazole B
by Yngve Guttormsen, Magnus E. Fairhurst, Sunil K. Pandey, Johan Isaksson, Bengt Erik Haug and Annette Bayer
Molecules 2020, 25(20), 4848; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25204848 - 21 Oct 2020
Cited by 4 | Viewed by 2894
Abstract
Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was developed. The synthesis [...] Read more.
Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was developed. The synthesis relied on the use of an oxazole precursor, which was protected with an iodine in the reactive 4-position, followed by complete chlorination of all pyrrole positions. Attempts to prepare phorbazole A and C, which contain a 3,4-dichlorinated pyrrole, were unsuccessful as the desired chlorination pattern on the pyrrole could not be obtained. The identities of the dichlorinated intermediates and products were determined using NMR techniques including NOESY/ROESY, 1,1-ADEQUATE and high-resolution CLIP-HSQMBC. Full article
(This article belongs to the Special Issue Total Synthesis of Natural Products)
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Review

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56 pages, 10900 KiB  
Review
The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly
by Nan Hu, Lorenzo V. White, Ping Lan and Martin G. Banwell
Molecules 2021, 26(3), 765; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26030765 - 02 Feb 2021
Cited by 5 | Viewed by 4094
Abstract
The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic [...] Read more.
The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic targets since the mid-1950s. Such efforts continue unabated and more recent studies on these alkaloids have focused on using them as vehicles for showcasing the utility of new synthetic methods. This review provides a comprehensive survey of the nearly seventy-year history of these synthetic endeavors. Full article
(This article belongs to the Special Issue Total Synthesis of Natural Products)
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45 pages, 20605 KiB  
Review
Synthesis of the Hexahydropyrrolo-[3,2-c]-quinoline Core Structure and Strategies for Further Elaboration to Martinelline, Martinellic Acid, Incargranine B, and Seneciobipyrrolidine
by Marianne B. Haarr and Magne O. Sydnes
Molecules 2021, 26(2), 341; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26020341 - 11 Jan 2021
Cited by 5 | Viewed by 3545
Abstract
Natural products are rich sources of interesting scaffolds possessing a plethora of biological activity. With the isolation of the martinella alkaloids in 1995, namely martinelline and martinellic acid, the pyrrolo[3,2-c]quinoline scaffold was discovered. Since then, this scaffold has been found in two additional [...] Read more.
Natural products are rich sources of interesting scaffolds possessing a plethora of biological activity. With the isolation of the martinella alkaloids in 1995, namely martinelline and martinellic acid, the pyrrolo[3,2-c]quinoline scaffold was discovered. Since then, this scaffold has been found in two additional natural products, viz. incargranine B and seneciobipyrrolidine. These natural products have attracted attention from synthetic chemists both due to the interesting scaffold they contain, but also due to the biological activity they possess. This review highlights the synthetic efforts made for the preparation of these alkaloids and formation of analogues with interesting biological activity. Full article
(This article belongs to the Special Issue Total Synthesis of Natural Products)
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