Article
Chemistry, Multidisciplinary
Yuan Jin, Kensuke Orihara, Fumiki Kawagishi, Tatsuya Toma, Tohru Fukuyama, Satoshi Yokoshima
Summary: The total synthesis of Haliclonin A was achieved through a series of reactions including Birch reduction/alkylation, ring-closing metathesis, intramolecular cyclopropanation, and stereoselective 1,4-addition, leading to the formation of the desired compound.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Georg Niggemeyer, Anastasia Knyazeva, Raphael Gasper, Dale Corkery, Pia Bodenbinder, Julian J. Holstein, Sonja Sievers, Yao-Wen Wu, Herbert Waldmann
Summary: Design and synthesis of pseudo-natural products through recombination of natural product fragments enables the discovery of novel biologically relevant chemical matter. In this study, the combination of this principle with macrocycle formation was described, leading to the efficient synthesis of 163 macrocyclic pseudo-natural products. Biological investigation revealed their potent inducers of autophagy-related processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Cedric Couturier, Sebastian Gross, Alexander von Tesmar, Judith Hoffmann, Selina Deckarm, Anouchka Fievet, Nelly Dubarry, Thomas Taillier, Christoph Poeverlein, Heike Stump, Michael Kurz, Luigi Toti, Sabine Haag Richter, Dietmar Schummer, Philippe Sizun, Michael Hoffmann, Ram Prasad Awal, Nestor Zaburannyi, Kirsten Harmrolfs, Joachim Wink, Emilie Lessoud, Thierry Vermat, Veronique Cazals, Sandra Silve, Armin Bauer, Michael Mourez, Laurent Fraisse, Corinne Leroi-Geissler, Astrid Rey, Stephanie Versluys, Eric Bacque, Rolf Mueller, Stephane Renard
Summary: This article describes the myxobacterial natural product Corramycin isolated from Corallococcus coralloides. Corramycin exhibits anti-Gram-negative activity against Escherichia coli and is taken up via two transporter systems. The biosynthetic gene cluster (BGC) of Corramycin was identified and a biosynthesis model was proposed. The absolute configuration of the molecule was elucidated through bioinformatic analysis and total synthesis. Animal experiments confirmed the antibacterial effect of Corramycin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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)
Article
Chemistry, Multidisciplinary
Nicholas L. Magann, Mitchell T. Blyth, Michael S. Sherburn
Summary: The concise synthesis of alkaloid lythranidine utilizes the target's C-2 symmetry, adopting a two directional synthetic approach to efficiently access gram quantities of the natural product. The broad-spectrum nature of the synthesis is demonstrated through the preparation of three diastereomeric analogues of the natural product.
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
Jiaxiang Wang, Jiahui Gao, Tianyun Guo, Xing Huo, Wenhua Zhang, Jian Liu, Xiaolei Wang
Summary: In this study, bioinspired total syntheses of A201A, A201D, and A201E were achieved based on a previously reported biosynthetic pathway. The challenging 1,2-cis-furanoside, a core structure of the A201 family, was obtained through remote 2-quinolinecarbonyl-assisted glycosylation. The total synthesis of A201A and A201E was accomplished without interference from basic dimethyl adenosine, and the absolute configuration of A201E was confirmed. This modular synthesis strategy allows efficient preparation of A201 family antibiotics, facilitating the study of their structure-activity relationships and mode of action.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chi He, Yu Wang, Cheng Bi, David S. Peters, Timothy J. Gallagher, Johannes Teske, Jason S. Chen, Rachel Corsetti, Anthony D'Onofrio, Kim Lewis, Phil S. Baran
Summary: A modular total synthesis method for kibdelomycin has been disclosed, which allows for structure-activity relationship studies. This method uses simple building blocks and addresses lingering questions regarding its structural assignment and its relationship to amycolamicin. Initial antibacterial assays indicate that both C-22 epimers of the natural product exhibit similar activity, while structurally truncated analogs lose activity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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)
Article
Chemistry, Multidisciplinary
Lorenz E. Loeffler, Conny Wirtz, Alois Fuerstner
Summary: This paper presents a new approach to chemical synthesis that allows for the preparation of a variety of casbane derivatives, especially the more highly oxygenated and arguably more relevant members of the family. Key design elements include catalyst-controlled intramolecular cyclopropanation, chain extension of stereoisomeric cyclopropane building blocks, and ring-closing alkyne metathesis. The concise total syntheses of depressin, yuexiandajisu A, and ent-pekinenin C demonstrate the effectiveness of this method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Annie R. Hooper, Andraz Ostrek, Ana Milian-Lopez, David Sarlah
Summary: This study presents a chemical synthesis method for preparing pyritide A2, involving the synthesis of a pyridine ring from an amino acid precursor, resulting in the efficient preparation of this class of natural products and analogues.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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, Multidisciplinary
Wenjun Huang, Shuai Fan, Jiahui Gao, Shangwen Luo, Shouchu Tang, Jian Liu, Xiaolei Wang
Summary: In this study, the de novo synthesis of miharamycin B was achieved, overcoming challenges such as the introduction of functional groups, stereoselective construction, and cyclization. This synthesis strategy enables efficient preparation of saccharides and facilitates the study of their structure-activity relationships and mode of action.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yeonghun Song, Jae Hyun Kim, Young Chan Kim, Sanghee Kim
Summary: Efforts towards the first total synthesis of (-)-oxazolomycin B and (+)-oxazolomycin C from the intermediate of our previous synthesis of (+)-neoxazolomycin are reported. The syntheses were achieved in a longest linear sequence of 25 steps from the amino acid serine in 3.6 and 2.7 % overall yields, respectively. The efficiency of our approach is derived from silyl triflate-mediated reductive oxazolidine ring-opening and Furstner's Ru-catalyzed hydrosilylation and protodesilylation reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
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, Physical
Xianwen Mao, Xiaoqing Yang, Jie Wu, Wenda Tian, Gregory C. Rutledge, T. Alan Hatton
CHEMISTRY OF MATERIALS
(2015)
Article
Chemistry, Multidisciplinary
Xianwen Mao, Wenda Tian, Jie Wu, Gregory C. Rutledge, T. Alan Hatton
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Zhi He, Minwoo Bae, Jie Wu, Timothy F. Jamison
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
Jie Wu, Xiaoqing Yang, Zhi He, Xianwen Mao, T. Alan Hatton, Timothy F. Jamison
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
Xiaoqing Yang, Jie Wu, Xianwen Mao, Timothy F. Jamison, T. Alan Hatton
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Multidisciplinary
Jennifer A. Kozak, Jie Wu, Xiao Su, Fritz Simeon, T. Alan Hatton, Timothy F. Jamison
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Multidisciplinary
Jie Wu, Jennifer A. Kozak, Fritz Simeon, T. Alan Hatton, Timothy F. Jamison
Meeting Abstract
Chemistry, Multidisciplinary
Bin Cai, Ryan Evans, Jie Wu
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Meeting Abstract
Chemistry, Multidisciplinary
Jie Wu, Xiaoqing Yang, Timothy F. Jamison, T. Alan Hatton
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Meeting Abstract
Chemistry, Multidisciplinary
Jie Wu, T. Alan Hatton, Timothy F. Jamison
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
