Special Issue "Catalyzed Synthesis of Natural Products"

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

Deadline for manuscript submissions: closed (30 April 2018)

Special Issue Editor

Guest Editor
Prof. Dr. David Díez

Department of Organic Chemistry, Universidad de Salamanca, Castilla y León, Salamanca 37008, Spain
Website | E-Mail
Phone: 0034923294500
Interests: Synthesis; Organic Synthesis; Synthetic Organic Chemistry; Medicinal and Pharmaceutical Chemistry

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

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Keywords

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

Published Papers (6 papers)

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Research

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Open AccessArticle Production of Structured Phosphatidylcholine with High Content of Myristic Acid by Lipase-Catalyzed Acidolysis and Interesterification
Catalysts 2018, 8(7), 281; https://doi.org/10.3390/catal8070281
Received: 6 June 2018 / Revised: 4 July 2018 / Accepted: 12 July 2018 / Published: 14 July 2018
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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
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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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Open AccessArticle Diastereoselective Synthesis of 7,8-Carvone Epoxides
Catalysts 2018, 8(6), 250; https://doi.org/10.3390/catal8060250
Received: 4 June 2018 / Revised: 15 June 2018 / Accepted: 16 June 2018 / Published: 19 June 2018
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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,
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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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Open AccessFeature PaperArticle Deep Eutectic Mixtures as Reaction Media for the Enantioselective Organocatalyzed α-Amination of 1,3-Dicarbonyl Compounds
Catalysts 2018, 8(5), 217; https://doi.org/10.3390/catal8050217
Received: 27 April 2018 / Revised: 15 May 2018 / Accepted: 16 May 2018 / Published: 18 May 2018
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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.
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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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Open AccessCommunication Catalytic Enantioselective Addition of Me2Zn to Isatins
Catalysts 2017, 7(12), 387; https://doi.org/10.3390/catal7120387
Received: 15 November 2017 / Revised: 7 December 2017 / Accepted: 8 December 2017 / Published: 13 December 2017
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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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Open AccessArticle Biotransformation of Ergostane Triterpenoid Antcin K from Antrodia cinnamomea by Soil-Isolated Psychrobacillus sp. AK 1817
Catalysts 2017, 7(10), 299; https://doi.org/10.3390/catal7100299
Received: 22 September 2017 / Revised: 2 October 2017 / Accepted: 3 October 2017 / Published: 11 October 2017
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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
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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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Open AccessReview Total Synthesis and Biological Evaluation of Phaeosphaerides
Catalysts 2018, 8(5), 206; https://doi.org/10.3390/catal8050206
Received: 26 April 2018 / Revised: 5 May 2018 / Accepted: 7 May 2018 / Published: 14 May 2018
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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
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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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