Review
Chemistry, Multidisciplinary
Lauren G. O'Neil, John F. Bower
Summary: Classical amination methods involve the reaction of a nitrogen nucleophile with an electrophilic carbon center; however, in recent years, umpoled strategies have gained traction where the nitrogen source acts as an electrophile. A wide range of electrophilic aminating agents are now available, and these underpin a range of powerful C-N bond-forming processes. In this Review, we highlight the strategic use of electrophilic aminating agents in total synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Debobrata Paul, Ashis Kundu, Sanu Saha, Rajib Kumar Goswami
Summary: This feature article highlights total synthesis as a reliable tool for confirming the structure of natural products. Despite advances in spectroscopic techniques, structural misassignments of natural products remain common. Recent case studies have shown that chemical synthesis can be used to revise the structures of natural products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Xikang Zheng, Yan Li, Mengtie Guan, Lingyue Wang, Shilong Wei, Yi-Cheng Li, Chin-Yuan Chang, Zhengren Xu
Summary: A unified strategy for the biomimetic total synthesis of the spiroindimicin family of natural products was reported. Key transformations include one-pot two-enzyme-catalyzed oxidative dimerization and regioselective bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Huilin Li, Jing Zhang, Xuegong She
Summary: This MiniReview demonstrates the achievements in the construction of the diquinane ring system in the past decade, discussing the strategic synthesis of the diquinane unit and its impact on the field of natural product total synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Haoran Dong, Dachao Hu, Benke Hong, Jin Wang, Xiaoguang Lei
Summary: The first total syntheses of four natural antibiotics, vermisporin, PF1052/AB4015-A, AB4015-L, AB4015-B, and one hydrogenated natural product derivative, AB4015-A2, featuring a tetramic acid bearing cis-decalin ring, are reported. The functionalized cis-decalin ring was constructed via a diastereoselective intramolecular Diels-Alder (IMDA) reaction, with a rare endo-boat transition state. The efficient installation of the sterically hindered epoxy group in vermisporin, PF1052/AB4015-A, and AB4015-L was achieved through an intramolecular neighboring-group-oriented strategy, and the desired tetramic acid structure was obtained through a one-pot aminolysis/Dieckmann condensation cascade using L-amino acid derivatives. The total synthesis allowed for the unequivocal verification of the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Soumik De, Aritra Kumar Dan, Raghaba Sahu, Sagarika Parida, Debadutta Das
Summary: Gold catalysis is a popular and highly innovative field in catalysis research, providing new approaches for chemical transformations from simple starting materials. The application of gold catalysis in the total synthesis of natural products has successfully addressed complex challenges and achieved significant progress.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Review
Chemistry, Organic
Takaaki Sato, Takahiro Suto, Yoshiyuki Nagashima, Shori Mukai, Noritaka Chida
Summary: Skipped dienes, found in various biologically active natural products, have relatively undeveloped synthesis methods compared to conjugated dienes due to challenges posed by the sp(3)-hybridized carbon between two olefins. Recent advances in the synthesis of skipped dienes for total synthesis of complex natural products are classified into three categories, focusing on methods to achieve both high stereoselectivity and convergency.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lukas Anton Wein, Klaus Wurst, Thomas Magauer
Summary: The study presented the construction of seven novel ent-trachylobane diterpenoids using a bioinspired synthetic strategy. Enantioselective and scalable access to five ent-trachylobanes was achieved in the first phase, with one compound produced on a 300 mg scale. Chemical C-H oxidation methods were then used in the second phase to selectively convert two higher functionalized ent-trachylobanes, revealing the potential and limitations of established protocols for complex molecule synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Xu-Kun Wang, Yue-Mei Jia, Yi-Xian Li, Chu-Yi Yu
Summary: A new antibiotic called pseudouridimycin with a unique mode of action against both Gram-positive and Gram-negative bacteria, including multidrug-resistant strains, was synthesized using an efficient and practical convergent strategy.
Review
Chemistry, Multidisciplinary
Suman Chakrabarty, Evan O. Romero, Joshua B. Pyser, Jessica A. Yazarians, Alison R. H. Narayan
Summary: The total synthesis of structurally complex natural products remains an exciting area of research, with recent advancements in biocatalysis allowing for the application of enzymes in constructing complex molecules. The utilization of enzymes alongside small molecule-based approaches has enabled concise chemoenzymatic routes to natural products, demonstrating the potential for selective oxidation reactions and late-stage diversification of complex scaffolds.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Kevin Rafael Sokol, Thomas Magauer
Summary: This review provides an overview of synthetic methods and strategies for constructing oxepin and dihydrooxepin motifs in the context of natural product synthesis, highlighting key steps of each example.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Lei Li, Li Shi, Kun Wei, Yu-Rong Yang
Summary: The first asymmetric total synthesis of (+)-quinocarcinamide (3), an enantiomer of the natural oxidation product from antitumor antibiotic (-)-quinocarcin (1), is described, involving key steps such as iridium-catalyzed asymmetric allylic amidation of racemic alcohol 9, olefin cross-metathesis, S(N)2' reaction to forge tetrahydroisoquinoline, and stereocontrolled 1,3-dipolar cycloaddition between azomethine ylide and tert-butyl acrylate to construct the diazabicyclo[3.2.1]octane ring.
Article
Chemistry, Medicinal
Min Woo Ha, Jonghoon Kim, Seung-Mann Paek
Summary: The discovery of novel marine natural products often leads to efforts in finding new therapeutic ingredients. Due to the complexity and uniqueness of substances produced in the marine environment, there have been cases where the structures were incorrectly assigned despite the use of modern chemical techniques. Organic chemical synthesis and thorough spectroscopic data inspection are crucial in refuting inaccuracies in proposed structures.
Article
Chemistry, Multidisciplinary
Soojun Park, Jiwoo Lee, Jae Hyun Kim, Yeji Jeong, Seokwoo Lee, Su Won Lee, Sanghee Kim
Summary: A concise total synthesis of salinosporamides and cinnabaramides was achieved through the combined use of memory of chirality and dynamic kinetic resolution principles, involving aldol reactions and hydrolysis reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Acoustics
Sasadhar Majhi
Summary: Total synthesis is a method for preparing complex natural products from simple materials, which plays a crucial role in confirming complex structures and preparing rare bioactive substances. The use of ultrasound as a non-polluting energy source in the synthesis of bioactive natural products highlights its potential in sustainable and pharmaceutical chemistry.
ULTRASONICS SONOCHEMISTRY
(2021)
Article
Crystallography
Ashraf A. Aly, Martin Nieger, Stefan Braese, Momtaz E. M. Bakheet
Summary: The X-ray structure analyses of four compounds were conducted, revealing strong intramolecular hydrogen bonds that play significant roles in their crystal packing.
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
(2023)
Article
Chemistry, Organic
Jehan Y. Al-Humaidi, A. A. Nayl, Mohamed M. Abdalla, Sobhi M. Gomha
Summary: This study synthesized and tested the in-vivo activity of different compounds, and found that triazolo-tetrazine derivatives have excellent anticonvulsant and CNS-depressant activities. Further structure-activity relationship studies demonstrated that electron-releasing groups increase activity while electron-withdrawing groups decrease activity.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Multidisciplinary
N. Maximilian Bojanowski, Aleksandra Vranic, Vincent Hahn, Pascal Rietz, Tobias Messer, Julian Brueckel, Christopher Barner-Kowollik, Eva Blasco, Stefan Braese, Martin Wegener
Summary: Recent studies have introduced a new generation of photoinitiators for 3D laser nanoprinting, replacing two-photon absorption with two-step absorption. This can now be achieved using inexpensive blue laser diodes instead of expensive femtosecond laser systems. Additionally, researchers are exploring alternative photoinitiators that can be excited by one-color two-step absorption and be de-excited by a different laser color.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Chun Li, Henrik Schopmans, Lukas Langer, Stefan Marschner, Abhinav Chandresh, Jochen Buerck, Youichi Tsuchiya, Adachi Chihaya, Wolfgang Wenzel, Stefan Braese, Mariana Kozlowska, Lars Heinke
Summary: Researchers have successfully prepared a crystalline film based on porphyrin with chiral properties and demonstrated excellent optoelectronic performance. By assembling in a metal-organic framework film, the porphyrin core becomes twisted and chiral. The close packing and crystalline order of the porphyrin cores in the film result in outstanding optoelectronic properties. Through exciting the Soret band of porphyrin, efficient photoconduction with a high On-Off ratio is achieved. Moreover, handedness-dependent circularly-polarized-light photoconduction is obtained. The combination of assembly-induced chirality with the rich porphyrin chemistry opens up possibilities for organic materials with exceptional chiral and optoelectronic properties.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Editorial Material
Chemistry, Multidisciplinary
Zahid Hassan, Stefan Braese
Summary: Engineering novel micro-/nanoscale systems and devices based on supramolecular assembly has tremendous potential, but controlling the size, shape, and arrangements without templates remains a challenge.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xujun Qiu, Julian Brueckel, Christoph Zippel, Martin Nieger, Frank Biedermann, Stefan Braese
Summary: In this article, a multifunctionalisable aryl azide, tris(4-azidophenyl)methanol, is reported. It can be used as a protecting group for thiols in peptoid synthesis and can be cleaved under mild reaction conditions via a Staudinger reduction. Additionally, the easily accessible aryl azide can be functionalised through copper-catalysed cycloaddition reactions, offering more possibilities for materials chemistry applications.
Article
Chemistry, Multidisciplinary
Hannes Kuehner, Louis Leyen, Zahid Hassan, Christof Woell, Stefan Brase
Summary: In this report, a modular synthesis approach towards a new series of non-centrosymmetric, dipolar 4,4'-bipyridines was described. The selective substitution on only one pyridyl motif that could contain electron-donating or electron-withdrawing groups causes electronic/steric effects on one nitrogen atom in 4,4'-bipyridines. This synthetic protocol was further applied to prepare azo-functionalized asymmetric bipyridines and non-centrosymmetric 4,4'-bipyridine N oxide scaffolds.
Article
Materials Science, Multidisciplinary
Ilona Wagner, Simon Spiegel, Julian Brueckel, Matthias Schwotzer, Alexander Welle, Martina H. H. Stenzel, Stefan Braese, Salma Begum, Manuel Tsotsalas
Summary: Surface engineering of MOF NPs using dynamic modification strategies enables the tailoring of PEG-grafted MOF NPs with improved colloidal stability and high dispersity, while maintaining their morphology and lattice crystallinity. The PEG-grafted MOF NPs show reduced adsorption of HSA protein compared to uncoated ones, indicating the potential for reducing nonspecific interactions and introducing targeting moieties for specific interactions. This approach expands the applications of colloidal MOF NPs in biologically relevant fields.
MACROMOLECULAR MATERIALS AND ENGINEERING
(2023)
Article
Materials Science, Multidisciplinary
Mirella Wawryszyn, Robin Wilhelm, John Kim, Xiaoyang Zhong, Jeffery E. Raymond, Richard Thelen, Vanessa Trouillet, Matthias Schwotzer, Stefan Braese, Do Hoon Kim, Nicholas L. Abbott, Joerg Lahann
Summary: In the past decade, the phosphorescence of metal-free confined polymer structures has gained attention due to their sustainability, low toxicity, and usage in sensing applications. This study presents the preparation of a free-standing array of nanofibers and compares their optical properties to films with identical composition. The nanofibers form laterally aligned membranes with a high internal order, hourglass-shaped features, and a long-lived emission in the blue region. This research is significant as it constitutes the first report of long-lived emission from solid-state poly(p-xylylenes) nanofibers, and these controlled polymer arrays have potential applications in organic sensors and optoelectronic devices.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Christin Bednarek, Ute Schepers, Franziska Thomas, Stefan Braese
Summary: With the development of bioconjugation chemistry in the past two decades, particularly highlighted by the Nobel Prize in 2022, the search for new applications has intensified, expanding the possibilities of these simple, specific, and high-yield reactions. The advancement of bioconjugation methods is expected to enhance the field of bioinstructive and bioadaptive materials science in the future. This article discusses the recent developments in coupling various biological entities, such as polysaccharides, oligonucleotides, peptides, and proteins, and explores the impact of bioconjugation reactions in materials science and 3D printing, along with their challenges and requirements.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Biochemistry & Molecular Biology
Essmat M. El-Sheref, Stefan Braese, Hendawy N. Tawfeek, Fatmah Ali Alasmary, Bahaa G. M. Youssif
Summary: The reaction between 4-azido-quinolin-2(1H)-ones and active methylene compounds was studied, leading to the synthesis of a series of 4-(1,2,3-triazol-1-yl)quinolin-2(1H)-ones. Compounds 3f-j showed potent antiproliferative activity and exhibited potential as multi-target inhibitors of EGFR, BRAF(V600E), and EGFR(T790M). Moreover, compounds 3g and 3h demonstrated caspase activation, down-regulation of antiapoptotic Bcl2, and promising antioxidant activity.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biotechnology & Applied Microbiology
Ismail M. Ahmed, Ahmed I. Abd-Elhamid, Ashraf A. Aly, Stefan Braese, AbdElAziz A. Nayl
Summary: Ni2+/Fe3+ LDH, (Ni-Fe-CO3 LDH) with Ni/Fe molar ratio 3.0 was synthesized by co -precipitation for the remediation of chromium (VI) and Alizarine Red-S (ARS-dye). The effects of hydrogen ion concentration, shaking time, ARS-dye and/or Cr(VI) concentration, and adsorbents mass on the process were studied. The results showed that Ni-Fe-CO3 LDH fitted well with the pseudo-second-order model, and Langmuir isotherm had a better adsorption effect on ARS-dye and Cr(VI).
ENVIRONMENTAL TECHNOLOGY & INNOVATION
(2023)
Article
Chemistry, Medicinal
Lamya H. Al-Wahaibi, Essmat M. El-Sheref, Alaa A. Hassan, S. Braese, M. Nieger, Bahaa G. M. Youssif, Mahmoud A. A. Ibrahim, Hendawy N. Tawfeek
Summary: 2,3,4-trisubstituted thiazoles 3a-i were successfully synthesized and their structures were determined. These compounds showed excellent antiproliferative activity without exhibiting cytotoxicity. The most potent derivatives, compounds 3a, 3c, 3d, and 3f, demonstrated strong antiproliferative activity against human cancer cell lines and also exhibited potent inhibition against EGFR and BRAF(V600E).
Article
Chemistry, Multidisciplinary
Steffen A. Otterbach, David Elsing, Alexander D. Schulz, Henrik Tappert, Wolfgang Wenzel, Mariana Kozlowska, Holger Roehm, Stefan Braese
Summary: In this study, eight different hole transport materials were synthesized via double CH activation. By varying the donor groups and pi-linkers, a wide range of ionization potentials (IPs) were achieved, demonstrating high customizability. One of the materials, DiPCP-2, showed good performance as a hole transport layer in PSCs, and its facile synthesis enables a cost reduction by two thirds.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Physical
Lena Pilz, Carsten Natzeck, Jonas Wohlgemuth, Nina Scheuermann, Simon Spiegel, Simon Osswald, Alexander Knebel, Stefan Braese, Christof Woell, Manuel Tsotsalas, Nicholaus Prasetya
Summary: This study presents a novel approach to enhance the properties of polymer membranes from MOFs through crosslinking of the organic linker molecules and subsequent metal-atom removal. The researchers automated the process and used machine learning optimization to ensure reproducibility and high quality of the resulting polymeric membranes. The SURMOF membranes showed improved gas selectivity after crosslinking, and the gas permeance could be restored to its initial condition after removing the metal centers. The resulting polymeric membrane outperforms commercially available polymer membranes for H2/CO2 gas separation.
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
