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Catalysts
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Catalyzed Synthesis of Natural Products
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Catalyzed Synthesis of Natural Products

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalytic Materials".

Deadline for manuscript submissions: closed (30 April 2018) | Viewed by 35967

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. David Díez

E-Mail Website
Guest Editor
Department of Organic Chemistry, Faculty of Chemical Sciences, University of Salamanca, Castilla y León, 37008 Salamanca, Spain
Interests: natural product transformations; organocatalysis; organic synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural products play pivotal roles not only in drug discovery, but in the transformation and synthesis of new material. The Organic Synthesis have been always next to natural products not only to corroborate their structure but too to obtain many derivatives in order to increase their activity and reduce secondary effects. In the last years, there has been a removed interest in doing the synthesis of natural products in a catalytic manner.This special issue collects original research papers, reviews and commentaries focused on the challenges for catalyzed synthesis of natural products. Submissions are welcome especially (but not exclusively) in the following areas:

Organocatalyzed synthesis of natural products;

Catalyzed synthesis of Natural Products with metals: this part could be divided into catalyzed by noble metals or first row metals;

Biocatalytic Synthesis of Natural Products: this part could be divided into using enzymes or using microorganisms.

Prof. Dr. David Díez
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. Catalysts is an international peer-reviewed open access monthly 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 2200 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

  • synthesis
  • catalysis
  • natural products
  • organocatalysis
  • biocatalysis
  • noble metals
  • first row metals
  • enzymes
  • microorganisms

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Published Papers (7 papers)

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Editorial

Jump to: Research, Review

2 pages, 167 KiB  
Editorial
Catalyzed Synthesis of Natural Products
by David Diez
Catalysts 2019, 9(11), 884; https://doi.org/10.3390/catal9110884 - 25 Oct 2019
Viewed by 1932
Abstract
Natural Products are secondary metabolites, that have been the inspiration for chemists and chemical biologists for many years and have a special relevance in the chemical space [...] Full article
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)

Research

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13 pages, 1600 KiB  
Article
Production of Structured Phosphatidylcholine with High Content of Myristic Acid by Lipase-Catalyzed Acidolysis and Interesterification
by Anna Chojnacka and Witold Gładkowski
Catalysts 2018, 8(7), 281; https://doi.org/10.3390/catal8070281 - 14 Jul 2018
Cited by 17 | Viewed by 5891
Abstract
Synthesis of structured phosphatidylcholine (PC) enriched with myristic acid (MA) was conducted by acidolysis and interesterification reactions using immobilized lipases as catalysts and two acyl donors: trimyristin (TMA) isolated from ground nutmeg, and myristic acid obtained by saponification of TMA. Screening experiments indicated [...] Read more.
Synthesis of structured phosphatidylcholine (PC) enriched with myristic acid (MA) was conducted by acidolysis and interesterification reactions using immobilized lipases as catalysts and two acyl donors: trimyristin (TMA) isolated from ground nutmeg, and myristic acid obtained by saponification of TMA. Screening experiments indicated that the most effective biocatalyst for interesterification was Rhizomucor miehei lipase (RML), whereas for acidolysis, the most active were Thermomyces lanuginosus lipase (TLL) and RML. The effect of the molar ratio of substrates (egg-yolk PC/acyl donor), enzyme loading, and different solvent on the incorporation of MA into PC and on PC recovery was studied. The maximal incorporation of MA (44 wt%) was achieved after 48 h of RML-catalyzed interesterification in hexane using substrates molar ratio (PC/trimyristin) 1/5 and 30% enzyme load. Comparable results were obtained in toluene with 1/3 substrates molar ratio. Interesterification of PC with trimyristin resulted in significantly higher MA incorporation than acidolysis with myristic acid, particularly in the reactions catalyzed by RML. Full article
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)
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12 pages, 1731 KiB  
Article
Diastereoselective Synthesis of 7,8-Carvone Epoxides
by Sofia Pombal, Ignacio E. Tobal, Alejandro M. Roncero, Jesus M. Rodilla, Narciso M. Garrido, Francisca Sanz, Alberto Esteban, Jaime Tostado, Rosalina F. Moro, Maria Jose Sexmero, Pablo G. Jambrina and David Diez
Catalysts 2018, 8(6), 250; https://doi.org/10.3390/catal8060250 - 19 Jun 2018
Cited by 4 | Viewed by 6282
Abstract
The synthesis of the two 7,8-epoxides of carvone has been attained using organocatalysis in a two-step synthetic route through a bromoester intermediate. Among the different reaction conditions tested for the bromination reaction, moderate yields and diastereoselection are achieved using proline, quinidine, and diphenylprolinol, [...] Read more.
The synthesis of the two 7,8-epoxides of carvone has been attained using organocatalysis in a two-step synthetic route through a bromoester intermediate. Among the different reaction conditions tested for the bromination reaction, moderate yields and diastereoselection are achieved using proline, quinidine, and diphenylprolinol, yielding the corresponding bromoesters that were transformed separately into their epoxides, obtaining the enantiopure products. Full article
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)
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11 pages, 5188 KiB  
Article
Deep Eutectic Mixtures as Reaction Media for the Enantioselective Organocatalyzed α-Amination of 1,3-Dicarbonyl Compounds
by Diego Ros Ñíguez, Pegah Khazaeli, Diego A. Alonso and Gabriela Guillena
Catalysts 2018, 8(5), 217; https://doi.org/10.3390/catal8050217 - 18 May 2018
Cited by 19 | Viewed by 5955
Abstract
The enantioselective α-amination of 1,3-dicarbonyl compounds has been performed using deep eutectic solvents (DES) as a reaction media and chiral 2-amino benzimidazole-derived compounds as a catalytic system. With this procedure, the use of toxic volatile organic compounds (VOCs) as reaction media is avoided. [...] Read more.
The enantioselective α-amination of 1,3-dicarbonyl compounds has been performed using deep eutectic solvents (DES) as a reaction media and chiral 2-amino benzimidazole-derived compounds as a catalytic system. With this procedure, the use of toxic volatile organic compounds (VOCs) as reaction media is avoided. Furthermore, highly functionalized chiral molecules, which are important intermediates for the natural product synthesis, are synthetized by an efficient and stereoselective protocol. Moreover, the reaction can be done on a preparative scale, with the recycling of the catalytic system being possible for at least five consecutive reaction runs. This procedure represents a cheap, simple, clean, and scalable method that meets most of the principles to be considered a green and sustainable process. Full article
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)
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1908 KiB  
Communication
Catalytic Enantioselective Addition of Me2Zn to Isatins
by Carlos Vila, Andrés Del Campo, Gonzalo Blay and José R. Pedro
Catalysts 2017, 7(12), 387; https://doi.org/10.3390/catal7120387 - 13 Dec 2017
Cited by 4 | Viewed by 5198
Abstract
Chiral α-hydroxyamide L5 derived from (S)-(+)-mandelic acid catalyzes the enantioselective addition of dimethylzinc to isatins affording the corresponding chiral 3-hydroxy-3-methyl-2-oxindoles with good yields and er up to 90:10. Furthermore, several chemical transformations were performed with the 3-hydroxy-2-oxindoles obtained. Full article
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)
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1681 KiB  
Article
Biotransformation of Ergostane Triterpenoid Antcin K from Antrodia cinnamomea by Soil-Isolated Psychrobacillus sp. AK 1817
by Chien-Min Chiang, Tzi-Yuan Wang, An-Ni Ke, Te-Sheng Chang and Jiumn-Yih Wu
Catalysts 2017, 7(10), 299; https://doi.org/10.3390/catal7100299 - 11 Oct 2017
Cited by 10 | Viewed by 5381
Abstract
Antcin K is one of the major ergostane triterpenoids from the fruiting bodies of Antrodia cinnamomea, a parasitic fungus that grows only on the inner heartwood wall of the aromatic tree Cinnamomum kanehirai Hay (Lauraceae). To search for strains that have the [...] Read more.
Antcin K is one of the major ergostane triterpenoids from the fruiting bodies of Antrodia cinnamomea, a parasitic fungus that grows only on the inner heartwood wall of the aromatic tree Cinnamomum kanehirai Hay (Lauraceae). To search for strains that have the ability to biotransform antcin K, a total of 4311 strains of soil bacteria were isolated, and their abilities to catalyze antcin K were determined by ultra-performance liquid chromatography analysis. One positive strain, AK 1817, was selected for functional studies. The strain was identified as Psychrobacillus sp., based on the DNA sequences of the 16S rRNA gene. The biotransformation metabolites were purified with the preparative high-performance liquid chromatography method and identified as antcamphin E and antcamphin F, respectively, based on the mass and nuclear magnetic resonance spectral data. The present study is the first to report the biotransformation of triterpenoids from A. cinnamomea (Antrodia cinnamomea). Full article
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)
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Review

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10 pages, 2290 KiB  
Review
Total Synthesis and Biological Evaluation of Phaeosphaerides
by Kenichi Kobayashi, Kosaku Tanaka and Hiroshi Kogen
Catalysts 2018, 8(5), 206; https://doi.org/10.3390/catal8050206 - 14 May 2018
Cited by 4 | Viewed by 4278
Abstract
This article reviews studies regarding the total synthesis of phaeosphaerides A and B, nitrogen-containing bicyclic natural products isolated from an endophytic fungus. Numerous synthetic efforts and an X-ray crystal structure analysis of phaeosphaeride A have enabled revision of its originally proposed structure. In [...] Read more.
This article reviews studies regarding the total synthesis of phaeosphaerides A and B, nitrogen-containing bicyclic natural products isolated from an endophytic fungus. Numerous synthetic efforts and an X-ray crystal structure analysis of phaeosphaeride A have enabled revision of its originally proposed structure. In addition, a successful protic acid-mediated transformation of phaeosphaeride A to phaeosphaeride B revealed the hypothetical biosynthesis of phaeosphaeride B from phaeosphaeride A. Structure–activity relationship studies of phaeosphaeride derivatives are also discussed. Full article
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)
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