Review
Chemistry, Medicinal
Uli Kazmaier, Lukas Junk
Summary: Ilamycins/rufomycins and cyclomarins are marine cycloheptapeptides produced by Streptomyces sp., showing potent activity against mycobacteria and Plasmodium falciparum. Their biosynthesis involves a special NRPS and can be modified to obtain derivatives with varying activities. The mechanisms of action against tuberculosis and malaria were discovered, and the SAR studies indicated potential areas for modification in the molecules without losing activity.
Article
Biochemistry & Molecular Biology
Xin Li, Jian Chen, Kaixuan Luo, Yishan Guo, Yongxing Deng, Xianli Li, Wenjing Chen, Zunnan Huang, Jianqiang Liu, Zhengzhi Wu, Cheng Tao
Summary: A flexible asymmetric synthesis of both enantiomers of euphopilolide and jolkinolide E was successfully achieved utilizing an intramolecular oxa-Pauson-Khand reaction. Furthermore, the anti-hepatocellular carcinoma activity of the synthesized compounds was evaluated, showing significant effects and providing valuable insight for the development of anti-HCC small molecule drugs.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mengmeng Xu, Min Hou, Haibing He, Shuanhu Gao
Summary: This study developed a new synthetic method for constructing aryltetralin lactone lignans and successfully synthesized several natural lignans using this methodology. The synthesized aglacins and small-molecule library created new opportunities for SAR studies of the podophyllotoxin family of natural products.
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, Medicinal
Jennifer Greve, Axel Mogk, Uli Kazmaier
Summary: Ilamycins/rufomycins are marine cycloheptapeptides containing unusual amino acids that show potent activity against multidrug-resistant strains of Mycobacterium tuberculosis. Derivative 26 of ilamycins displays activity and has dual effects on the regulation of ClpC1 protease activity.
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, Organic
Harry B. Hicks, Daniel S. Brown, Hau Sun Sam Chan, Bruno A. Sousa, Kirsten E. Christensen, Jonathan W. Burton
Summary: In this study, the synthesis of both (E)-ocellenyne and (Z)-ocellenyne was reported, and their absolute configuration was determined through single crystal X-ray diffraction studies. The configuration of the syn-12,13-dibromide was found to be (S, S), supporting the proposed biogenesis from the (6S, 7S)-laurediols.
Article
Biochemistry & Molecular Biology
Rafael Baptista, Sumana Bhowmick, Jianying Shen, Luis A. J. Mur
Summary: In this study, a molecular reverse docking approach was used to predict interactions between 53 selected anti-mycobacterial natural products and known druggable mycobacterial targets. Results showed that certain compounds had significantly higher binding free energies against PknB and DprE1 targets, suggesting their potential use in drug optimization research.
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
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
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, 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, Medicinal
Hong-Xiu Xiao, Qing-Xiang Yan, Zhi-Hui He, Zheng-Biao Zou, Qing-Qing Le, Ting-Ting Chen, Bing Cai, Xian-Wen Yang, Su-Lan Luo
Summary: The first total synthesis of marine natural product, (-)-majusculoic acid, and its analogs showed potential anti-inflammatory activity with some compounds displaying significant inhibition rates. These compounds did not exhibit cytotoxicity, suggesting they may be promising anti-inflammatory agents.
Article
Chemistry, Organic
Min Wang, Zhoujie Xie, Shoubin Tang, Ee Ling Chang, Yue Tang, Zhengyan Guo, Yinglu Cui, Bian Wu, Tao Ye, Yihua Chen
Article
Chemistry, Organic
Mingze Yang, Wenquan Peng, Yian Guo, Tao Ye
Article
Chemistry, Medicinal
Fusong Wu, Tao Zhang, Jie Yu, Yian Guo, Tao Ye
Summary: The asymmetric total synthesis of four diastereomers of laingolide A enabled the unambiguous assignment of the natural product's stereochemistry. The key features of the convergent, fully stereocontrolled approach included a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination, and an RCM/alkene migration sequence to obtain the desired macrocyclic enamide.
Article
Chemistry, Organic
Yulu Jiang, Taro Ozaki, Chengwei Liu, Yuya Igarashi, Ying Ye, Shoubin Tang, Tao Ye, Jun-Ichi Maruyama, Atsushi Minami, Hideaki Oikawa
Summary: In the biosynthetic pathway of mycotoxin cyclochlorotine, DUF3328 proteins mediate various tailoring processes, including chlorination and hydroxylation, demonstrating a much higher functional diversity than previously expected.
Article
Chemistry, Multidisciplinary
Junya Takino, Akari Kotani, Taro Ozaki, Wenquan Peng, Jie Yu, Yian Guo, Susumu Mochizuki, Kazuya Akimitsu, Masaru Hashimoto, Tao Ye, Atsushi Minami, Hideaki Oikawa
Summary: Highly reducing polyketide synthases (HR-PKSs) are responsible for the production of structurally diverse polyketides (PKs) through a complex stereochemical process. By examining the synthesis of polyhydroxy PKs, researchers were able to determine the absolute configurations of stereogenic centers using chemical degradation and comparison with synthetic standards. This study proposes a stereochemical rule to explain the absolute configurations of reduced PKs and highlights discrepancies in previously reported structures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Fusong Wu, Jie Yu, Jiawei Meng, Yian Guo, Tao Ye
Summary: The first total synthesis of thiazole-containing cyclic depsipeptide pagoamide A has been achieved through a 9-step liquid-phase synthesis from simple known starting materials, confirming its structure unambiguously.
Article
Neurosciences
Lulu Yao, Yi Rong, Xiaoyan Ma, Haifu Li, Di Deng, Yongjun Chen, Sungchil Yang, Tao Peng, Tao Ye, Feixue Liang, Nenggui Xu, Qiang Zhou
Summary: NMDA subtype glutamate receptors play bidirectional roles in modulating the intrinsic excitability of inhibitory GABAergic neurons, depending on the subunit composition of NMDARs. These findings highlight the importance of NMDARs in inhibitory neurons and contribute to a better understanding of brain diseases.
JOURNAL OF NEUROSCIENCE
(2022)
Article
Chemistry, Organic
Junyang Liu, Ying Chen, Hendrik Luesch, Tao Ye
Summary: The first asymmetric total synthesis and validation of the structural assignment of des-thiomethyllooekeyolide A (3) is described, which involves a Shiina macrolactonization and a late-stage pyran-hemiketal formation. The eight stereogenic centers of the C16-polyketide chain were installed by sequential aldol and crotylation reactions.
Article
Biochemistry & Molecular Biology
Junyang Liu, Shoubin Tang, Jia-Lei Yan, Tao Ye
Summary: A novel hydrogen bond surrogate-based alpha-helix mimetic was designed using covalent H-bond replacement and an ether linkage to substitute an amide bond. CD studies showed that the mimetic maintained stable conformations in aqueous buffer at high temperatures.
Article
Biochemistry & Molecular Biology
Jing Chen, Yangyang Jiang, Jialei Yan, Chao Xu, Tao Ye
Summary: The first total syntheses of cyclic depsipeptides colletopeptide A and colletotrichamide A have been achieved through a series of transformations. By constructing a cyclic tridepsipeptide derivative as a key intermediate, followed by late-stage incorporation of the mannose fragment, the synthesis of colletotrichamide A and desilylation of the common intermediate led to the confirmation of the absolute stereochemistry of the natural products.
Article
Biochemistry & Molecular Biology
Xiaoyun Liao, Shupeng Li, Yian Guo, Tao Ye
Summary: The total synthesis of noursamycin A has been achieved, which proves that the original structural assignments were incorrect. The synthetic strategy described in this paper has also been utilized for the first total synthesis of nicrophorusamide A, a cyclopeptide that shares structural similarities with noursamycin A.
Article
Chemistry, Organic
Dacheng Wang, Pengwei Li, Jia-Lei Yan, Huijin Mao, Lilu Liu, Min Wang, Meng Chen, Tao Ye, Yihua Chen
Summary: In this study, the stereochemical structures of ARTs A and B were determined through a combination of spectroscopic, computational, and biosynthetic studies. Biosynthetic investigations played a crucial role in determining the absolute configuration of ART A and provided key evidence for the configuration of ART B's 3-ketosugar moiety, highlighting their importance in resolving the complex structures of natural products.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yi Xiao, Yangyang Jiang, Chao Xu, Pratanphorn Nakliang, Sanghee Yoon, Sun Choi, Yian Guo, Tao Ye
Summary: The stereocontrolled total synthesis of the antitumor natural product thioamycolamide A has been achieved in 14 steps with an overall yield of 19.1%. The key aspect of our approach is the preparation of the beta-alkylthio amide subunit through an auxiliary-controlled, diastereoselective sulfa-Michael addition.
ORGANIC CHEMISTRY FRONTIERS
(2022)
