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Special Issue "Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday"

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

Deadline for manuscript submissions: 31 October 2019.

Special Issue Editor

Prof. Dr. Ari Koskinen
E-Mail Website
Guest Editor
Department of Chemistry, Laboratory of Organic Chemistry, Aalto School of Chemical Technology
Interests: organic synthesis; asymmetric synthesis; natural products

Special Issue Information

Dear Colleagues,

Professor Dr. Dieter Schinzer, born 7 July, 1953 in Gudensberg, Germany, obtained his undergraduate education at the University of Marburg (1974–1977), whereafter he carried out his graduate studies at the University of Bonn under the supervision of Professor Manfred T. Reetz. In 1980, having obtained his PhD, he spent two years as a Feodor-Lynen post-doctoral fellow at the University of California, Berkeley in the research group of professor Clayton Heathcock. Upon returning to Germany, he obtained a Liebig fellowship and, at the Leibniz University of Hannover, finished his habilitation in 1986 with Professor Ekkehardt Winterfeldt. After another three years at Hannover as a Heisenberg fellow, Dr. Schinzer spent a year at the University of Göttingen (as the Schöllkopf Chair) followed by a period as a Visiting Professor at the University of Wisconsin, USA. In 1990 he was appointed Associate Professor of Chemistry at the Technical University of Braunschweig before receiving a full professorship for the Otto-von-Guericke University of Magdeburg Institute of Chemistry in 1997, his current position. Here he served as the Dean of the Faculty of Chemical Engineering from 2002 to 2005.

Despite his wide research interests in organometallic chemistry (especially silicon, tin and manganese), synthetic methodology and medicinal chemistry, Dr. Schinzer is first and foremost a devoted natural product chemist. In 1997, his research group was among the first to achieve the total synthesis of epothilones. His interest in medicinal chemistry led him to be a founder and CSO of MOLISA (Molecular Links Sachsen-Anhalt GmbH) in 2002. He was then instrumental in developing several European COST research consortia under the general umbrella of Bioactive Natural Product synthesis. He also served as the Chairman of the COST Domain Committee for Chemistry and Molecular Sciences from 2006 to 2009.

Molecules is pleased to announce a Special Issue honoring Dr. Dieter Schinzer, on the occasion of his 65th birthday, for his outstanding achievements in natural product chemistry. This Special Issue is dedicated to all aspects of natural product chemistry, in particular total synthesis, but, following the interests of Dr. Schinzer, contributions related to isolation and structure elucidation, as well as drug design based on natural product leads, their computer aided methods and structure-activity relationships (SAR), are welcome.

It is a pleasure to invite you to submit a manuscript to this Special Issue. Regular articles, communications, and reviews are all welcome.

Prof. Dr. Ari Koskinen
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 papers will be 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 1800 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
  • Total synthesis
  • Bioinspired drug design
  • Isolation
  • Structure elucidation
  • Bioactivity
  • Structure–activity relationships

Published Papers (6 papers)

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Research

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Open AccessFeature PaperArticle
Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate
Molecules 2019, 24(19), 3477; https://doi.org/10.3390/molecules24193477 - 25 Sep 2019
Abstract
The total synthesis of (+)-10-keto-oxycodone was attained from phenethyl acetate in a stereoselective manner. Absolute stereochemistry was established via enzymatic dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) that furnished the corresponding cis-cyclohexadienediol whose configuration corresponds to the absolute stereochemistry [...] Read more.
The total synthesis of (+)-10-keto-oxycodone was attained from phenethyl acetate in a stereoselective manner. Absolute stereochemistry was established via enzymatic dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) that furnished the corresponding cis-cyclohexadienediol whose configuration corresponds to the absolute stereochemistry of the ring C of (+)-10-keto-oxycodone. Intramolecular Heck reaction was utilized to establish the quaternary carbon at C-13, along with the dibenzodihydrofuran functionality. The C-14 hydroxyl and C-10 ketone were installed via SmI2-mediated radical cyclization, and oxidation of a benzylic alcohol (obtained from an intermediate nitrate azide), respectively. The synthesis of (+)-10-keto-oxycodone was completed in a total of 14 operations (21 steps) and an overall yield of ~2%. Experimental and spectral data are provided for key intermediates and new compounds. Full article
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Open AccessArticle
Synthesis, Structural Confirmation, and Biosynthesis of 22-OH-PD1n-3 DPA
Molecules 2019, 24(18), 3228; https://doi.org/10.3390/molecules24183228 - 05 Sep 2019
Abstract
PD1n-3 DPA belongs to the protectin family of specialized pro-resolving lipid mediators. The protectins are endogenously formed mediators that display potent anti-inflammatory properties and pro-resolving bioactivities and have attracted interest in drug discovery. However, few studies have been reported of the secondary [...] Read more.
PD1n-3 DPA belongs to the protectin family of specialized pro-resolving lipid mediators. The protectins are endogenously formed mediators that display potent anti-inflammatory properties and pro-resolving bioactivities and have attracted interest in drug discovery. However, few studies have been reported of the secondary metabolism of the protectins. To investigate the metabolic formation of the putative C22 mono-hydroxylated product, coined 22-OH-PD1n-3 DPA, a stereoselective synthesis was performed. LC/MS-MS data of synthetic 22-OH-PD1n-3 DPA matched the data for the biosynthetic formed product. Cellular studies revealed that 22-OH-PD1n-3 DPA is formed from n-3 docosapentaenoic acid in human serum, and we confirmed that 22-OH-PD1n-3 DPA is a secondary metabolite produced by ω-oxidation of PD1n-3 DPA in human neutrophils and in human monocytes. The results reported are of interest for enabling future structure–activity relationship studies and provide useful molecular insight of the metabolism of the protectin class of specialized pro-resolving mediators. Full article
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Open AccessArticle
Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling
Molecules 2019, 24(14), 2654; https://doi.org/10.3390/molecules24142654 - 22 Jul 2019
Abstract
A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a [...] Read more.
A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a vinylic iodide and an aldehyde. Good yields of carbocyclic products were obtained from the reaction, but diastereomeric mixtures of allylic alcohols were produced. The cyclisation reaction was successful irrespective of the relative configuration of the stereogenic centres in the cyclisation precursor. Full article
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Review

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Open AccessReview
Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes
Molecules 2019, 24(18), 3412; https://doi.org/10.3390/molecules24183412 - 19 Sep 2019
Abstract
Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due [...] Read more.
Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due to their extensive application of organocatalysis in the total synthesis of bioactive molecules and some of them have been used in the industrial synthesis of drugs have attracted increasing interests from chemists. Among the chiral organocatalysts, chiral secondary amines (MacMillan’s catalyst and Jorgensen’s catalyst) have been especially considered attractive strategies because of their impressive efficiency. Herein, we outline advances in the asymmetric total synthesis of natural products and relevant drugs by using the strategy of chiral secondary amine catalyzed reactions of α,β-unsaturated aldehydes in the last eighteen years. Full article
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Open AccessReview
Chemical and Biocatalytic Routes to Arbutin
Molecules 2019, 24(18), 3303; https://doi.org/10.3390/molecules24183303 - 11 Sep 2019
Abstract
Arbutin (also called β-arbutin) is a natural product occurring in the leaves of a variety of different plants, the bearberries of the Ericaceae and Saxifragaceae families being prominent examples. It is a β-glucoside derived from hydroquinone (HQ; 1,4-dihydroxybenzene). Arbutin has been identified in [...] Read more.
Arbutin (also called β-arbutin) is a natural product occurring in the leaves of a variety of different plants, the bearberries of the Ericaceae and Saxifragaceae families being prominent examples. It is a β-glucoside derived from hydroquinone (HQ; 1,4-dihydroxybenzene). Arbutin has been identified in traditional Chinese folk medicines as having, inter alia, anti-microbial, anti-oxidant, and anti-inflammatory properties that useful in the treatment of different ailments including urinary diseases. Today, it is also used worldwide for the treatment of skin ailments by way of depigmenting, which means that arbutin is a component of many products in the cosmetics and healthcare industries. It is also relevant in the food industry. Hundreds of publications have appeared describing the isolation, structure determination, toxicology, synthesis, and biological properties of arbutin as well as the molecular mechanism of melanogenesis (tyrosinase inhibition). This review covers the most important aspects with special emphasis on the chemical and biocatalytic methods for the production of arbutin. Full article
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Open AccessReview
Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
Molecules 2019, 24(17), 3040; https://doi.org/10.3390/molecules24173040 - 22 Aug 2019
Abstract
It is a challenging objective in synthetic organic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated into the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction [...] Read more.
It is a challenging objective in synthetic organic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated into the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction is the most important transformation to generate this structural element as it not only creates new C–C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies of aldol and aldol-type reactions have been put forward. In this regard, the vinylogous Mukaiyama aldol reaction (VMAR) became a pivotal transformation as it allows the synthesis of larger fragments while incorporating 1,5-relationships and generating two new stereocenters and one double bond simultaneously. This review summarizes and updates methodology-oriented and target-oriented research focused on the various aspects of the vinylogous Mukaiyama aldol (VMA) reaction. This manuscript comprehensively condenses the last four years of research, covering the period 2016–2019. Full article

Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Author: Martin Cordes and Markus Kalesse
Institute of Organic Chemistry, Gottfried Wilhelm Leibniz University of Hannover, Schneiderberg 1b,
6 30167 Hannover, Germany

Paper type: Review
Tentative Title: Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
Tentative abstract: It is a challenging objective in synthetic organic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated in the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction as the most important transformation to generate this structural element not only creates new C–C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies of aldol and aldol-type reactions had been put forward. On this background, the vinylogous Mukaiyama aldol reaction (here and hereafter VMAR) became a pivotal transformation since it allows the synthesis of larger fragments while incorporating 1,5-relationships and generating two new stereocenters and one double bond simultaneously. This review summarizes and updates methodology-oriented and target-oriented researches focused on the various aspects of the VMA reaction. The manuscript comprehensively condenses the last four
20 years of research, covering the period 2016–2019.

 

Author: Kenichi Kobayashi, Risako Kunimura, and Hiroshi Kogen
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Paper type: Communication
Tentative Title: Total synthesis of the proposed structure of paraphaeosphaeride C
Tentative abstract: Paraphaeosphaeride C is a nitrogen-containing bicyclic natural product with STAT3 inhibitory activity, which is a demethoxy derivative of phaeosphaeride A. In our previous papers, we reported the total synthesis of phaeosphaeride A by a diastereoselective vinyl anion aldol reaction as a key step to construct a dihydropyran ring. In this work, the first total synthesis of the proposed structure of paraphaeosphaeride C was achieved by a similar synthetic strategy to that used for phaeosphaeride A. The synthetic compound was characterized through extended NMR analysis, however, 1H and 13C NMR data for this compound did not correspond to those reported in the literature for paraphaeosphaeride C.

 

 

 

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