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

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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: closed (31 July 2020) | Viewed by 62632

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Prof. Dr. Ari Koskinen

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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
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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

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Keywords

Natural products
Total synthesis
Bioinspired drug design
Isolation
Structure elucidation
Bioactivity
Structure–activity relationships

Published Papers (13 papers)

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Editorial

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4 pages, 183 KiB

Open AccessEditorial

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

by Ari M. P. Koskinen

Molecules 2020, 25(24), 5841; https://doi.org/10.3390/molecules25245841 - 10 Dec 2020

Viewed by 1376

Abstract

Natural products have intrigued humans throughout history [...] Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

Research

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27 pages, 6089 KiB

Open AccessArticle

Ring-Closing Metathesis Approaches towards the Total Synthesis of Rhizoxins

by Marc Liniger, Christian M. Neuhaus and Karl-Heinz Altmann

Molecules 2020, 25(19), 4527; https://doi.org/10.3390/molecules25194527 - 02 Oct 2020

Cited by 5 | Viewed by 3975

Abstract

Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ring-closure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F. Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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10 pages, 2131 KiB

Open AccessArticle

First Synthesis of (−)-Altenuene-D₃ Suitable as Internal Standard for Isotope Dilution Mass Spectrometry

by Michael A. Sebald, Julian Gebauer, Thomas Sommerfeld and Matthias Koch

Molecules 2019, 24(24), 4563; https://doi.org/10.3390/molecules24244563 - 12 Dec 2019

Cited by 3 | Viewed by 2531

Abstract

Metabolites from Alternaria fungi exhibit a variety of biological properties such as phytotoxic, cytotoxic, or antimicrobial activity. Optimization of a literature procedure culminated in an efficient total synthesis of (−)-altenuene as well as a stable isotope-labeled derivative suitable for implementation in a [...] Read more.

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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Graphical abstract

9 pages, 2680 KiB

Open AccessCommunication

Total Synthesis of the Proposed Structure of Paraphaeosphaeride C

by Kenichi Kobayashi, Risako Kunimura and Hiroshi Kogen

Molecules 2019, 24(23), 4230; https://doi.org/10.3390/molecules24234230 - 21 Nov 2019

Cited by 2 | Viewed by 2379

Abstract

Paraphaeosphaeride C is a demethoxy derivative of phaeosphaeride A and exhibits STAT3 inhibitory activity. Our previous papers reported the total synthesis of phaeosphaeride A using a diastereoselective vinyl anion aldol reaction as the key step to construct the dihydropyran ring. In this work, the first total synthesis of the proposed structure of paraphaeosphaeride C was achieved via a similar synthetic strategy. The synthetic compound was characterized through extensive nuclear magnetic resonance (NMR) analysis but the ¹H and ¹³C-NMR data for this compound did not correspond to those reported in the literature for paraphaeosphaeride C. Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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12 pages, 2350 KiB

Open AccessFeature PaperArticle

Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate

by Mary Ann Endoma-Arias, Helen Dela Paz and Tomas Hudlicky

Molecules 2019, 24(19), 3477; https://doi.org/10.3390/molecules24193477 - 25 Sep 2019

Cited by 9 | Viewed by 4950

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 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

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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13 pages, 1697 KiB

Open AccessArticle

Synthesis, Structural Confirmation, and Biosynthesis of 22-OH-PD1_{n-3 DPA}

by Jannicke Irina Nesman, Karoline Gangestad Primdahl, Jørn Eivind Tungen, Fransesco Palmas, Jesmond Dalli and Trond Vidar Hansen

Molecules 2019, 24(18), 3228; https://doi.org/10.3390/molecules24183228 - 05 Sep 2019

Cited by 9 | Viewed by 3550

Abstract

PD1_{n-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-PD1_{n-3 DPA}, a stereoselective synthesis was performed. LC/MS-MS data of synthetic 22-OH-PD1_{n-3 DPA} matched the data for the biosynthetic formed product. Cellular studies revealed that 22-OH-PD1_{n-3 DPA} is formed from n-3 docosapentaenoic acid in human serum, and we confirmed that 22-OH-PD1_{n-3 DPA} is a secondary metabolite produced by ω-oxidation of PD1_{n-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

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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15 pages, 1458 KiB

Open AccessArticle

Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling

by Anthony Aimon, Louis J. Farrugia and J. Stephen Clark

Molecules 2019, 24(14), 2654; https://doi.org/10.3390/molecules24142654 - 22 Jul 2019

Cited by 6 | Viewed by 4125

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 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

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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Review

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34 pages, 16478 KiB

Open AccessReview

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

by Satya Kumar Avula, Biswanath Das, Rene Csuk, Ahmed Al-Rawahi and Ahmed Al-Harrasi

Molecules 2020, 25(8), 1905; https://doi.org/10.3390/molecules25081905 - 20 Apr 2020

Cited by 5 | Viewed by 3957

Abstract

Pyranone natural products have attracted great attention in recent years from chemists and biologists due to their fascinating stereoisomeric structural features and impressive bioactivities. A large number of stereoselective total syntheses of these compounds have been described in the literature. The natural pyranones with long side chains have recently received significant importance in the synthetic field. In the present article, we aim to review the modern progress of the stereoselective total syntheses of these natural pyranones containing long-chain substituents. Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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82 pages, 37510 KiB

Open AccessReview

The Pictet-Spengler Reaction Updates Its Habits

by Andrea Calcaterra, Laura Mangiardi, Giuliano Delle Monache, Deborah Quaglio, Silvia Balducci, Simone Berardozzi, Antonia Iazzetti, Roberta Franzini, Bruno Botta and Francesca Ghirga

Molecules 2020, 25(2), 414; https://doi.org/10.3390/molecules25020414 - 19 Jan 2020

Cited by 55 | Viewed by 11410

Abstract

The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations. Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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38 pages, 10970 KiB

Open AccessReview

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

by Zhonglei Wang

Molecules 2019, 24(18), 3412; https://doi.org/10.3390/molecules24183412 - 19 Sep 2019

Cited by 24 | Viewed by 7433

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 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

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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9 pages, 2629 KiB

Open AccessReview

Chemical and Biocatalytic Routes to Arbutin ^†

by Hangyu Zhou, Jing Zhao, Aitao Li and Manfred T. Reetz

Molecules 2019, 24(18), 3303; https://doi.org/10.3390/molecules24183303 - 11 Sep 2019

Cited by 26 | Viewed by 6585

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 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

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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19 pages, 3971 KiB

Open AccessReview

Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis

by Martin Cordes and Markus Kalesse

Molecules 2019, 24(17), 3040; https://doi.org/10.3390/molecules24173040 - 22 Aug 2019

Cited by 20 | Viewed by 5632

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 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

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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Other

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11 pages, 2920 KiB

Open AccessFeature PaperConcept Paper

Some Biogenetic Considerations Regarding the Marine Natural Product (−)-Mucosin

by Jens M. J. Nolsøe, Marius Aursnes, Yngve H. Stenstrøm and Trond V. Hansen

Molecules 2019, 24(22), 4147; https://doi.org/10.3390/molecules24224147 - 15 Nov 2019

Cited by 5 | Viewed by 3563

Abstract

Recently, the identity of the marine hydrindane natural product (−)-mucosin was revised to the trans-fused structure 6, thereby providing a biogenetic puzzle that remains to be solved. We are now disseminating some of our insights with regard to the possible machinery delivering the established architecture. Aspects with regard to various modes of cyclization in terms of concerted versus stepwise processes are held up against the enzymatic apparatus known to be working on arachidonic acid (8). To provide a contrast to the tentative polyunsaturated fatty acid biogenesis, the structural pattern featured in (−)-mucosin (6) is compared to some marine hydrinane natural products of professed polyketide descent. Our appraisal points to a different origin and strengthens the hypothesis of a polyunsaturated fatty acids (PUFA) as the progenitor of (−)-mucosin (6). Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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