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
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
Livia Dikosova, Barbora Otoskova, Tomas Malatinsky, Jana Dohanosova, Maria Kopacova, Anna Durinova, Lucie Smutna, Frantisek Trejtnar, Robert Fischer
Summary: This study successfully synthesized two polyhydroxylated pyrrolizidine alkaloids using a specific synthetic method, confirming their structure, stereochemistry, and biological activity. This research has the potential to provide important insights for further studies in related fields.
Article
Biochemistry & Molecular Biology
Rudrakshula Madhavachary, Rosy Mallik, Dhevalapally B. Ramachary
Summary: In this study, biologically important, chiral natural products of butenolides and their analogues were successfully synthesized in very good yields using a sequential one-pot method, featuring key steps of organocatalytic reductive coupling and either palladium-mediated reductive deoxygenation or silica-mediated reductive deamination.
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
Prabhakara R. Tharra, Andrey A. Mikhaylov, Jiri Svejkar, Marina Gysin, Sven N. Hobbie, Jakub Svenda
Summary: We report a concise synthesis method for the naturally occurring protein synthesis inhibitor (+)-actinobolin. The complex molecular structure of 1 was assembled using (-)-quinic acid, L-threonine, and L-alanine. Our simplified synthesis route, consisting of 9 steps with 18% overall yield, has practical applications for analog preparation, as shown in this study.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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, Organic
Brendan J. Byatt, Atsushi Kato, Stephen G. Pyne
Summary: The iminosugar core of natural glyphaeaside C, originally thought to be a derivative of DNJ, has been revised as a derivative of L-DMDP through the total synthesis of its enantiomer. This novel L-DMDP-derived configuration is the first of its kind observed in nature, and the prepared iminosugars showed nanomolar inhibition of bovine liver beta-glucosidase and beta-galactosidase.
Article
Chemistry, Organic
Stergios R. Rizos, Konstantinos A. Ouzounthanasis, Alexandros E. Koumbis
Summary: The research focused on synthesizing Chabrolobenzoquinone H, a meroditerpene metabolite with cytotoxic activity, and determining its absolute configuration securely.
JOURNAL OF ORGANIC CHEMISTRY
(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
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, 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
Cedric Tresse, Marc Francois-Heude, Vincent Servajean, Rubal Ravinder, Clemence Lesieur, Lucie Geiben, Louis Jeanne-Julien, Vincent Steinmetz, Pascal Retailleau, Emmanuel Roulland, Jean-Marie Beau, Stephanie Norsikian
Summary: The total synthesis of tiacumicin B was achieved by utilizing glycosylation steps and Suzuki-Miyaura cross-coupling. Unique glycosylation steps and macrolactonization techniques were used to successfully synthesize tiacumicin B.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
