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Synthesis and Structure−Activity Correlation of Natural-Product Inspired Cyclodepsipeptides Stabilizing F-Actin

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Max-Planck-Institut für molekulare Physiologie, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany, and Technische Universität Dortmund Fakultät Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
[email protected]; [email protected]
Cite this: J. Am. Chem. Soc. 2010, 132, 9, 3063–3077
Publication Date (Web):February 11, 2010
https://doi.org/10.1021/ja9095126
Copyright © 2010 American Chemical Society
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    Abstract

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    The fundamental role played by actin in the regulation of eukaryotic cell maintenance and motility renders it a primary target for small-molecule intervention. In this arena, a class of potent cytotoxic cyclodepsipeptide natural products has emerged over the last quarter-century to stimulate the fields of biology and chemistry with their unique actin-stabilizing properties and complex peptide−polyketide hybrid structures. Despite considerable research effort, a structural basis for the activity of these secondary metabolites remains elusive, not least for the lack of high-resolution structural data and a reliable synthetic route to diverse compound libraries. In response to this, an efficient solid-phase approach has been developed and successfully applied to the total synthesis of jasplakinolide and chondramide C and diverse analogues. The key macrocylization step was realized using ruthenium-catalyzed ring-closing metathesis (RCM) that in the course of a library synthesis produced discernible trends in metathesis reactivity and E/Z-selectivity. After optimization, the RCM step could be operated under mild conditions, a result that promises to facilitate the synthesis of more extensive analogue libraries for structure−function studies. The growth inhibitory effects of the synthesized compounds were quantified and structure−activity correlations established which appear to be in good alignment with relevant biological data from natural products. In this way a number of potent unnatural and simplified analogues have been found. Furthermore, potentially important stereochemical and structural components of a common pharmacophore have been identified and rationalized using molecular modeling. These data will guide in-depth mode-of-action studies, especially into the relationship between the cytotoxicity of these compounds and their actin-perturbing properties, and should inform the future design of simplified and functionalized actin stabilizers as well.

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    Detailed experimental (synthetic and cell screening) procedures, comprehensive compound characterization, including copies of 1H NMR and 13C NMR spectral data, molecular modeling data, additional graphical representation and numbering convention for peptide diene 23n and macrocyclic structures E-28a, Z-28a, E-29a, Z-29a, E-30c, and E-31c. This material is available free of charge via the Internet at http://pubs.acs.org.

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    2. Vladimir N. Belov, Stefan Stoldt, Franziska Rüttger, Michael John, Jan Seikowski, Jens Schimpfhauser, Stefan W. Hell. Synthesis of Fluorescent Jasplakinolide Analogues for Live-Cell STED Microscopy of Actin. The Journal of Organic Chemistry 2020, 85 (11) , 7267-7275. https://doi.org/10.1021/acs.joc.0c00653
    3. Stéphanie M. Guéret, Sasikala Thavam, Rodrigo J. Carbajo, Marco Potowski, Niklas Larsson, Göran Dahl, Anita Dellsén, Tom N. Grossmann, Alleyn T. Plowright, Eric Valeur, Malin Lemurell, Herbert Waldmann. Macrocyclic Modalities Combining Peptide Epitopes and Natural Product Fragments. Journal of the American Chemical Society 2020, 142 (10) , 4904-4915. https://doi.org/10.1021/jacs.0c00269
    4. Solomon D. Appavoo, Sungjoon Huh, Diego B. Diaz, Andrei K. Yudin. Conformational Control of Macrocycles by Remote Structural Modification. Chemical Reviews 2019, 119 (17) , 9724-9752. https://doi.org/10.1021/acs.chemrev.8b00742
    5. Hiroaki Itoh, Masayuki Inoue. Comprehensive Structure–Activity Relationship Studies of Macrocyclic Natural Products Enabled by Their Total Syntheses. Chemical Reviews 2019, 119 (17) , 10002-10031. https://doi.org/10.1021/acs.chemrev.9b00063
    6. Lu Wang, Michelle S. Frei, Aleksandar Salim, Kai Johnsson. Small-Molecule Fluorescent Probes for Live-Cell Super-Resolution Microscopy. Journal of the American Chemical Society 2019, 141 (7) , 2770-2781. https://doi.org/10.1021/jacs.8b11134
    7. Yajie Wang, Mark J. Bartlett, Carl A. Denard, John F. Hartwig, and Huimin Zhao . Combining Rh-Catalyzed Diazocoupling and Enzymatic Reduction To Efficiently Synthesize Enantioenriched 2-Substituted Succinate Derivatives. ACS Catalysis 2017, 7 (4) , 2548-2552. https://doi.org/10.1021/acscatal.7b00254
    8. Zhantao Yang, Xiaolong Xu, Chun-Hua Yang, Yunfeng Tian, Xinyi Chen, Lihui Lian, Wenwei Pan, Xuncheng Su, Weicheng Zhang, and Yue Chen . Total Synthesis of Nannocystin A. Organic Letters 2016, 18 (21) , 5768-5770. https://doi.org/10.1021/acs.orglett.6b02729
    9. Kristin N. Bauer, Hisaschi T. Tee, Ingo Lieberwirth, and Frederik R. Wurm . In-Chain Poly(phosphonate)s via Acyclic Diene Metathesis Polycondensation. Macromolecules 2016, 49 (10) , 3761-3768. https://doi.org/10.1021/acs.macromol.6b00366
    10. Sayantan Das and Rajib Kumar Goswami . Stereoselective Total Synthesis of Marine Cyclodepsipeptide Calcaripeptides A–C. The Journal of Organic Chemistry 2014, 79 (20) , 9778-9791. https://doi.org/10.1021/jo5019798
    11. Lech-Gustav Milroy, Tom N. Grossmann, Sven Hennig, Luc Brunsveld, and Christian Ottmann . Modulators of Protein–Protein Interactions. Chemical Reviews 2014, 114 (9) , 4695-4748. https://doi.org/10.1021/cr400698c
    12. Thomas Classen, Margarete Korpak, Melanie Schölzel, and Jörg Pietruszka . Stereoselective Enzyme Cascades: An Efficient Synthesis of Chiral γ-Butyrolactones. ACS Catalysis 2014, 4 (5) , 1321-1331. https://doi.org/10.1021/cs5000262
    13. Paulami Danner, Marius Morkunas, and Martin E. Maier . Synthesis of d-Abrines by Palladium-catalyzed Reaction of ortho-Iodoanilines with N-Boc-N-methylalanyl-substituted Acetaldehyde and Acetylene. Organic Letters 2013, 15 (10) , 2474-2477. https://doi.org/10.1021/ol4009409
    14. Lech-Gustav Milroy, Stefano Rizzo, Abram Calderon, Bernhard Ellinger, Silke Erdmann, Justine Mondry, Peter Verveer, Philippe Bastiaens, Herbert Waldmann, Leif Dehmelt, and Hans-Dieter Arndt . Selective Chemical Imaging of Static Actin in Live Cells. Journal of the American Chemical Society 2012, 134 (20) , 8480-8486. https://doi.org/10.1021/ja211708z
    15. Jonathan Sorres, Marie-Thérèse Martin, Sylvain Petek, Hélène Levaique, Thierry Cresteil, Suzanne Ramos, Odile Thoison, Cécile Debitus, and Ali Al-Mourabit . Pipestelides A–C: Cyclodepsipeptides from the Pacific Marine Sponge Pipestela candelabra. Journal of Natural Products 2012, 75 (4) , 759-763. https://doi.org/10.1021/np200714m
    16. Wenbo Pei and Isaac J. Krauss . Homoallylboration and Homocrotylboration of Aldehydes. Journal of the American Chemical Society 2011, 133 (46) , 18514-18517. https://doi.org/10.1021/ja2048682
    17. Tao Xu, Chuang-chuang Li, and Zhen Yang . A Concise Approach for the Total Synthesis of Pseudolaric Acid A. Organic Letters 2011, 13 (10) , 2630-2633. https://doi.org/10.1021/ol200741j
    18. Francisco Sarabia, Samy Chammaa, and Cristina García-Ruiz . Solid Phase Synthesis of Globomycin and SF-1902 A5. The Journal of Organic Chemistry 2011, 76 (7) , 2132-2144. https://doi.org/10.1021/jo1025145
    19. Katharine R. Watts, Brandon I. Morinaka, Taro Amagata, Sarah J. Robinson, Karen Tenney, Walter M. Bray, Nadine C. Gassner, R. Scott Lokey, Joseph Media, Frederick A. Valeriote, and Phillip Crews . Biostructural Features of Additional Jasplakinolide (Jaspamide) Analogues. Journal of Natural Products 2011, 74 (3) , 341-351. https://doi.org/10.1021/np100721g
    20. Jonas Bucevičius, Rūta Gerasimaitė, Kamila A. Kiszka, Shalini Pradhan, Georgij Kostiuk, Tanja Koenen, Gražvydas Lukinavičius. A general highly efficient synthesis of biocompatible rhodamine dyes and probes for live-cell multicolor nanoscopy. Nature Communications 2023, 14 (1) https://doi.org/10.1038/s41467-023-36913-2
    21. Prima F. Hillman, Chaeyoung Lee, Sang-Jip Nam. Microbial Natural Products with Wound-Healing Properties. Processes 2023, 11 (1) , 30. https://doi.org/10.3390/pr11010030
    22. Florian Küllmer, Nynke A. Vepřek, Malgorzata Borowiak, Veselin Nasufović, Sebastian Barutzki, Oliver Thorn‐Seshold, Hans‐Dieter Arndt, Dirk Trauner. Next Generation Opto‐Jasplakinolides Enable Local Remodeling of Actin Networks**. Angewandte Chemie 2022, 134 (48) https://doi.org/10.1002/ange.202210220
    23. Florian Küllmer, Nynke A. Vepřek, Malgorzata Borowiak, Veselin Nasufović, Sebastian Barutzki, Oliver Thorn‐Seshold, Hans‐Dieter Arndt, Dirk Trauner. Next Generation Opto‐Jasplakinolides Enable Local Remodeling of Actin Networks**. Angewandte Chemie International Edition 2022, 61 (48) https://doi.org/10.1002/anie.202210220
    24. Jia-Xiang Lv, Ya-Qi Ding, Chen-Ming Huang, Ling-Ling Guo, Jia-Li Fang, Xian Jia, Wen-He Zhang, Song You, Bin Qin. Enzyme- and Chemo-enzyme-Catalyzed Stereodivergent Synthesis. Pharmaceutical Fronts 2022, 04 (03) , e121-e135. https://doi.org/10.1055/s-0042-1755556
    25. Veselin Nasufović, Florian Küllmer, Johanna Bößneck, Hans‐Martin Dahse, Helmar Görls, Peter Bellstedt, Pierre Stallforth, Hans‐Dieter Arndt. Total Synthesis and Bioactivity Mapping of Geodiamolide H. Chemistry – A European Journal 2021, 27 (45) , 11633-11642. https://doi.org/10.1002/chem.202100989
    26. Anna Kajetanowicz, Karol Grela. Durch Nitro‐ und andere elektronenziehende Gruppen aktivierte Ruthenium‐Katalysatoren für die Olefinmetathese. Angewandte Chemie 2021, 133 (25) , 13854-13873. https://doi.org/10.1002/ange.202008150
    27. Anna Kajetanowicz, Karol Grela. Nitro and Other Electron Withdrawing Group Activated Ruthenium Catalysts for Olefin Metathesis Reactions. Angewandte Chemie International Edition 2021, 60 (25) , 13738-13756. https://doi.org/10.1002/anie.202008150
    28. Sabrina Pospich, Florian Küllmer, Veselin Nasufović, Johanna Funk, Alexander Belyy, Peter Bieling, Hans‐Dieter Arndt, Stefan Raunser. Cryo‐EM Resolves Molecular Recognition Of An Optojasp Photoswitch Bound To Actin Filaments In Both Switch States. Angewandte Chemie 2021, 133 (16) , 8760-8764. https://doi.org/10.1002/ange.202013193
    29. Sabrina Pospich, Florian Küllmer, Veselin Nasufović, Johanna Funk, Alexander Belyy, Peter Bieling, Hans‐Dieter Arndt, Stefan Raunser. Cryo‐EM Resolves Molecular Recognition Of An Optojasp Photoswitch Bound To Actin Filaments In Both Switch States. Angewandte Chemie International Edition 2021, 60 (16) , 8678-8682. https://doi.org/10.1002/anie.202013193
    30. Qiang Wu, Yingying Jing, Tan Zhao, Jing Gao, Mingjun Cai, Haijiao Xu, Yi Liu, Feng Liang, Junling Chen, Hongda Wang. Development of small molecule inhibitor-based fluorescent probes for highly specific super-resolution imaging. Nanoscale 2020, 12 (42) , 21591-21598. https://doi.org/10.1039/D0NR05188H
    31. Rūta Gerasimaitė, Jan Seikowski, Jens Schimpfhauser, Georgij Kostiuk, Tanja Gilat, Elisa D'Este, Sebastian Schnorrenberg, Gražvydas Lukinavičius. Efflux pump insensitive rhodamine–jasplakinolide conjugates for G- and F-actin imaging in living cells. Organic & Biomolecular Chemistry 2020, 18 (15) , 2929-2937. https://doi.org/10.1039/D0OB00369G
    32. Shuaijun Wang, Alvaro H. Crevenna, Ilke Ugur, Antoine Marion, Iris Antes, Uli Kazmaier, Maria Hoyer, Don C. Lamb, Florian Gegenfurtner, Zane Kliesmete, Christoph Ziegenhain, Wolfgang Enard, Angelika Vollmar, Stefan Zahler. Actin stabilizing compounds show specific biological effects due to their binding mode. Scientific Reports 2019, 9 (1) https://doi.org/10.1038/s41598-019-46282-w
    33. Daniel Reker, Gonçalo J. L. Bernardes, Tiago Rodrigues. Computational advances in combating colloidal aggregation in drug discovery. Nature Chemistry 2019, 11 (5) , 402-418. https://doi.org/10.1038/s41557-019-0234-9
    34. Yunfeng Tian, Jiyan Wang, Wenjie Liu, Xiaoya Yuan, Yang Tang, Jing Li, Yue Chen, Weicheng Zhang. Stereodivergent total synthesis of Br-nannocystins underpinning the polyketide (10R,11S) configuration as a key determinant of potency. Journal of Molecular Structure 2019, 1181 , 568-578. https://doi.org/10.1016/j.molstruc.2018.12.107
    35. Jintao Xu, Lei Hu. Asymmetric one-pot synthesis of five- and six-membered lactones via dynamic covalent kinetic resolution: Exploring the regio- and stereoselectivities of lipase. Tetrahedron Letters 2019, 60 (12) , 868-871. https://doi.org/10.1016/j.tetlet.2019.02.030
    36. Philipp Ermert, Anatol Luther, Peter Zbinden, Daniel Obrecht. Frontier Between Cyclic Peptides and Macrocycles. 2019, 147-202. https://doi.org/10.1007/978-1-4939-9504-2_9
    37. Jan Hendrik Lang, Thomas Lindel. Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling. Beilstein Journal of Organic Chemistry 2019, 15 , 577-583. https://doi.org/10.3762/bjoc.15.53
    38. Dan Georgess, Pirjo Spuul, Christophe Le Clainche, Damien Le Nihouannen, Isabelle Fremaux, Thierry Dakhli, Daniela Melanie Delannoy López, Denis Deffieux, Pierre Jurdic, Stéphane Quideau, Elisabeth Génot. Anti-osteoclastic effects of C-glucosidic ellagitannins mediated by actin perturbation. European Journal of Cell Biology 2018, 97 (8) , 533-545. https://doi.org/10.1016/j.ejcb.2018.09.003
    39. Yunfeng Tian, Yahui Ding, Xiaolong Xu, Yanju Bai, Yang Tang, Xin Hao, Weicheng Zhang, Yue Chen. Total synthesis and biological evaluation of nannocystin analogues modified at the polyketide phenyl moiety. Tetrahedron Letters 2018, 59 (33) , 3206-3209. https://doi.org/10.1016/j.tetlet.2018.07.028
    40. Felipe Merino, Sabrina Pospich, Johanna Funk, Thorsten Wagner, Florian Küllmer, Hans-Dieter Arndt, Peter Bieling, Stefan Raunser. Structural transitions of F-actin upon ATP hydrolysis at near-atomic resolution revealed by cryo-EM. Nature Structural & Molecular Biology 2018, 25 (6) , 528-537. https://doi.org/10.1038/s41594-018-0074-0
    41. Yunfeng Tian, Xiaolong Xu, Yahui Ding, Xin Hao, Yanju Bai, Yang Tang, Xuemei Zhang, Qiuying Li, Zhantao Yang, Weicheng Zhang, Yue Chen. Synthesis and biological evaluation of nannocystin analogues toward understanding the binding role of the (2R,3S)-Epoxide in nannocystin A. European Journal of Medicinal Chemistry 2018, 150 , 626-632. https://doi.org/10.1016/j.ejmech.2018.03.012
    42. Sabrina Pospich, Esa-Pekka Kumpula, Julian von der Ecken, Juha Vahokoski, Inari Kursula, Stefan Raunser. Near-atomic structure of jasplakinolide-stabilized malaria parasite F-actin reveals the structural basis of filament instability. Proceedings of the National Academy of Sciences 2017, 114 (40) , 10636-10641. https://doi.org/10.1073/pnas.1707506114
    43. Eric Valeur, Stéphanie M. Guéret, Hélène Adihou, Ranganath Gopalakrishnan, Malin Lemurell, Herbert Waldmann, Tom N. Grossmann, Alleyn T. Plowright. Neue Modalitäten für schwierige Zielstrukturen in der Wirkstoffentwicklung. Angewandte Chemie 2017, 129 (35) , 10428-10459. https://doi.org/10.1002/ange.201611914
    44. Eric Valeur, Stéphanie M. Guéret, Hélène Adihou, Ranganath Gopalakrishnan, Malin Lemurell, Herbert Waldmann, Tom N. Grossmann, Alleyn T. Plowright. New Modalities for Challenging Targets in Drug Discovery. Angewandte Chemie International Edition 2017, 56 (35) , 10294-10323. https://doi.org/10.1002/anie.201611914
    45. Aneta Gandalovičová, Daniel Rosel, Michael Fernandes, Pavel Veselý, Petr Heneberg, Vladimír Čermák, Luboš Petruželka, Sunil Kumar, Victoria Sanz-Moreno, Jan Brábek. Migrastatics—Anti-metastatic and Anti-invasion Drugs: Promises and Challenges. Trends in Cancer 2017, 3 (6) , 391-406. https://doi.org/10.1016/j.trecan.2017.04.008
    46. Jaehee Lee, Sebastian Torker, Amir H. Hoveyda. Versatile Homoallylic Boronates by Chemo‐, S N 2′‐, Diastereo‐ and Enantioselective Catalytic Sequence of Cu−H Addition to Vinyl‐B(pin)/Allylic Substitution. Angewandte Chemie 2017, 129 (3) , 839-844. https://doi.org/10.1002/ange.201611444
    47. Jaehee Lee, Sebastian Torker, Amir H. Hoveyda. Versatile Homoallylic Boronates by Chemo‐, S N 2′‐, Diastereo‐ and Enantioselective Catalytic Sequence of Cu−H Addition to Vinyl‐B(pin)/Allylic Substitution. Angewandte Chemie International Edition 2017, 56 (3) , 821-826. https://doi.org/10.1002/anie.201611444
    48. Enza Lacivita, Ermelinda Lucente, Chantal Kwizera, Ines F. Antunes, Mauro Niso, Paola De Giorgio, Roberto Perrone, Nicola A. Colabufo, Philip H. Elsinga, Marcello Leopoldo. Structure-activity relationship study towards non-peptidic positron emission tomography (PET) radiotracer for gastrin releasing peptide receptors: Development of [18F] (S)-3-(1H-indol-3-yl)-N-[1-[5-(2-fluoroethoxy)pyridin-2-yl]cyclohexylmethyl]-2-methyl-2-[3-(4-nitrophenyl)ureido]propionamide. Bioorganic & Medicinal Chemistry 2017, 25 (1) , 277-292. https://doi.org/10.1016/j.bmc.2016.10.031
    49. Magnus W. P. Bebbington. Natural product analogues: towards a blueprint for analogue-focused synthesis. Chemical Society Reviews 2017, 46 (16) , 5059-5109. https://doi.org/10.1039/C6CS00842A
    50. Xiaoting Wu, Fang Xie, Zheng Ling, Liang Tang, Wanbin Zhang. Regio‐ and Enantioselective Copper‐Catalyzed 1,4‐Conjugate Addition of Trimethylaluminium to Linear α,β,γ,δ‐Unsaturated Alkyl Ketones. Advanced Synthesis & Catalysis 2016, 358 (15) , 2510-2518. https://doi.org/10.1002/adsc.201600375
    51. Larry Yet. Olefin Ring‐Closing Metathesis. 2016, 1-1304. https://doi.org/10.1002/0471264180.or089.01
    52. Daniel J. Tetlow, Steve J. Winder, Christophe Aïssa. The synthesis and biological evaluation of a kabiramide C fragment modified with a WH2 consensus actin-binding motif as a potential disruptor of the actin cytoskeleton. Chemical Communications 2016, 52 (4) , 807-810. https://doi.org/10.1039/C5CC06081H
    53. Irene Notar Francesco, Bastien Cacciuttolo, Oana Pascu, Cyril Aymonier, Mathieu Pucheault, Sylvain Antoniotti. Simple salts of abundant metals (Fe, Bi, and Ti) supported on montmorillonite as efficient and recyclable catalysts for regioselective intramolecular and intermolecular hydroalkoxylation reactions of double bonds and tandem processes. RSC Advances 2016, 6 (24) , 19807-19818. https://doi.org/10.1039/C5RA25176A
    54. Dominic Becker, Uli Kazmaier. Synthesis and Biological Evaluation of Dichlorinated Chondramide Derivatives. European Journal of Organic Chemistry 2015, 2015 (19) , 4198-4213. https://doi.org/10.1002/ejoc.201500369
    55. Hans‐Dieter Arndt, Stefano Rizzo, Christina Nöcker, Vijay N. Wakchaure, Lech‐Gustav Milroy, Vanessa Bieker, Abram Calderon, Tuyen T. N. Tran, Silke Brand, Leif Dehmelt, Herbert Waldmann. Divergent Solid‐Phase Synthesis of Natural Product‐Inspired Bipartite Cyclodepsipeptides: Total Synthesis of Seragamide A. Chemistry – A European Journal 2015, 21 (14) , 5311-5316. https://doi.org/10.1002/chem.201500368
    56. C. Rademacher, P. H. Seeberger. High-Throughput Synthesis of Diverse Compound Collections for Lead Discovery and Optimization. 2015, 73-89. https://doi.org/10.1007/164_2015_25
    57. Ana Gradillas, Javier Pérez-Castells. Synthesis of Macrocycles Other than Peptides by Metathesis. 2015, 245-318. https://doi.org/10.1007/7081_2015_151
    58. Toshiyuki Kowada, Hiroki Maeda, Kazuya Kikuchi. BODIPY-based probes for the fluorescence imaging of biomolecules in living cells. Chemical Society Reviews 2015, 44 (14) , 4953-4972. https://doi.org/10.1039/C5CS00030K
    59. Martin E. Maier. Design and synthesis of analogues of natural products. Organic & Biomolecular Chemistry 2015, 13 (19) , 5302-5343. https://doi.org/10.1039/C5OB00169B
    60. Phillip J. Unsworth, Daniele Leonori, Varinder K. Aggarwal. Stereocontrolled Synthesis of 1,5‐Stereogenic Centers through Three‐Carbon Homologation of Boronic Esters. Angewandte Chemie 2014, 126 (37) , 10004-10008. https://doi.org/10.1002/ange.201405700
    61. Phillip J. Unsworth, Daniele Leonori, Varinder K. Aggarwal. Stereocontrolled Synthesis of 1,5‐Stereogenic Centers through Three‐Carbon Homologation of Boronic Esters. Angewandte Chemie International Edition 2014, 53 (37) , 9846-9850. https://doi.org/10.1002/anie.201405700
    62. Sandip Sengupta, Taebo Sim. A Concise Synthesis of Mupirocin H Using a Cross‐Metathesis‐Based Strategy. European Journal of Organic Chemistry 2014, 2014 (23) , 5063-5070. https://doi.org/10.1002/ejoc.201402442
    63. James J. La Clair, Steven T. Loveridge, Karen Tenney, Mark O'Neil–Johnson, Eli Chapman, Phillip Crews, . In Situ Natural Product Discovery via an Artificial Marine Sponge. PLoS ONE 2014, 9 (7) , e100474. https://doi.org/10.1371/journal.pone.0100474
    64. Rosa Cookson, Christoph Pöverlein, Jennifer Lachs, Anthony G. M. Barrett. Synthetic Studies towards Radicicol through Biomimetic Macrolactonization and Transannular Aromatization Reactions. European Journal of Organic Chemistry 2014, 2014 (21) , 4523-4535. https://doi.org/10.1002/ejoc.201402205
    65. Jigang Wang, Xing Fei Tan, Van Sang Nguyen, Peng Yang, Jing Zhou, Mingming Gao, Zhengjun Li, Teck Kwang Lim, Yingke He, Chye Sun Ong, Yifei Lay, Jianbin Zhang, Guili Zhu, Siew-Li Lai, Dipanjana Ghosh, Yu Keung Mok, Han-Ming Shen, Qingsong Lin. A Quantitative Chemical Proteomics Approach to Profile the Specific Cellular Targets of Andrographolide, a Promising Anticancer Agent That Suppresses Tumor Metastasis. Molecular & Cellular Proteomics 2014, 13 (3) , 876-886. https://doi.org/10.1074/mcp.M113.029793
    66. Gregory Roos. Alkylation and Related Reactions II. 2014, 69-172. https://doi.org/10.1016/B978-0-12-417034-6.00003-7
    67. Gábor Tasnádi, Mélanie Hall. Relevant Practical Applications of Bioreduction Processes in the Synthesis of Active Pharmaceutical Ingredients. 2013, 329-374. https://doi.org/10.1002/9783527665785.ch13
    68. Jennifer Herrmann, Stephan Hüttel, Rolf Müller. Discovery and Biological Activity of New Chondramides from Chondromyces sp.. ChemBioChem 2013, 14 (13) , 1573-1580. https://doi.org/10.1002/cbic.201300140
    69. Haruhiko Fuwa, Masato Kawakami, Kenkichi Noto, Takashi Muto, Yuto Suga, Keiichi Konoki, Mari Yotsu‐Yamashita, Makoto Sasaki. Concise Synthesis and Biological Assessment of (+)‐Neopeltolide and a 16‐Member Stereoisomer Library of 8,9‐Dehydroneopeltolide: Identification of Pharmacophoric Elements. Chemistry – A European Journal 2013, 19 (25) , 8100-8110. https://doi.org/10.1002/chem.201300664
    70. Wamtinga Sawadogo, Marc Schumacher, Marie-Hélène Teiten, Claudia Cerella, Mario Dicato, Marc Diederich. A Survey of Marine Natural Compounds and Their Derivatives with Anti-Cancer Activity Reported in 2011. Molecules 2013, 18 (4) , 3641-3673. https://doi.org/10.3390/molecules18043641
    71. Karen Schweikart, Liang Guo, Zachary Shuler, Rory Abrams, Eric T. Chiao, Kyle L. Kolaja, Myrtle Davis. The effects of jaspamide on human cardiomyocyte function and cardiac ion channel activity. Toxicology in Vitro 2013, 27 (2) , 745-751. https://doi.org/10.1016/j.tiv.2012.12.005
    72. Igor A. Schepetkin, Liliya N. Kirpotina, Andrei I. Khlebnikov, Marcello Leopoldo, Ermelinda Lucente, Enza Lacivita, Paola De Giorgio, Mark T. Quinn. 3-(1H-indol-3-yl)-2-[3-(4-nitrophenyl)ureido]propanamide enantiomers with human formyl-peptide receptor agonist activity: Molecular modeling of chiral recognition by FPR2. Biochemical Pharmacology 2013, 85 (3) , 404-416. https://doi.org/10.1016/j.bcp.2012.11.015
    73. Kiran Matcha, Ashoka V. R. Madduri, Sayantani Roy, Slava Ziegler, Herbert Waldmann, Anna K. H. Hirsch, Adriaan J. Minnaard. Total Synthesis of (−)‐Doliculide, Structure–Activity Relationship Studies and Its Binding to F‐Actin. ChemBioChem 2012, 13 (17) , 2537-2548. https://doi.org/10.1002/cbic.201200512
    74. Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, James E. Thomson. The conjugate addition of enantiomerically pure lithium amides as chiral ammonia equivalents part II: 2005−2011. Tetrahedron: Asymmetry 2012, 23 (15-16) , 1111-1153. https://doi.org/10.1016/j.tetasy.2012.08.009
    75. James W. Herndon. The chemistry of the carbon–transition metal double and triple bond: Annual survey covering the year 2010. Coordination Chemistry Reviews 2012, 256 (13-14) , 1281-1376. https://doi.org/10.1016/j.ccr.2012.02.015
    76. Gorakh S. Yellol, Chung‐Ming Sun. Solid‐Supported Synthesis. 2012, 393-442. https://doi.org/10.1002/9780470711828.ch15
    77. Barry M. Trost, David J. Michaelis, Julie Charpentier, Jiayi Xu. Palladium‐Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N ‐Acyloxazolinones as Ester Enolate Equivalents. Angewandte Chemie 2012, 124 (1) , 208-212. https://doi.org/10.1002/ange.201105801
    78. Barry M. Trost, David J. Michaelis, Julie Charpentier, Jiayi Xu. Palladium‐Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N ‐Acyloxazolinones as Ester Enolate Equivalents. Angewandte Chemie International Edition 2012, 51 (1) , 204-208. https://doi.org/10.1002/anie.201105801
    79. Khanh Ha, Jean-Christophe M. Monbaliu, Byron C. Williams, Girinath G. Pillai, Charles E. Ocampo, Matthias Zeller, Christian V. Stevens, Alan R. Katritzky. A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure. Organic & Biomolecular Chemistry 2012, 10 (40) , 8055. https://doi.org/10.1039/c2ob25996f
    80. Alexander Zhdanko, Anke Schmauder, Christopher I. Ma, L. David Sibley, David Sept, Florenz Sasse, Martin E. Maier. Synthesis of Chondramide A Analogues with Modified β‐Tyrosine and Their Biological Evaluation. Chemistry – A European Journal 2011, 17 (47) , 13349-13357. https://doi.org/10.1002/chem.201101978
    81. Stefan Wetzel, Robin S. Bon, Kamal Kumar, Herbert Waldmann. Biologie‐orientierte Synthese (BIOS). Angewandte Chemie 2011, 123 (46) , 10990-11018. https://doi.org/10.1002/ange.201007004
    82. Stefan Wetzel, Robin S. Bon, Kamal Kumar, Herbert Waldmann. Biology‐Oriented Synthesis. Angewandte Chemie International Edition 2011, 50 (46) , 10800-10826. https://doi.org/10.1002/anie.201007004
    83. Margarete Korpak, Jörg Pietruszka. Chemoenzymatic One‐Pot Synthesis of γ‐Butyrolactones. Advanced Synthesis & Catalysis 2011, 353 (9) , 1420-1424. https://doi.org/10.1002/adsc.201100110
    84. Stéphane Quideau, Céline Douat‐Casassus, Daniela Melanie Delannoy López, Carmelo Di Primo, Stefan Chassaing, Rémi Jacquet, Frédéric Saltel, Elisabeth Genot. Binding of Filamentous Actin and Winding into Fibrillar Aggregates by the Polyphenolic C‐Glucosidic Ellagitannin Vescalagin. Angewandte Chemie 2011, 123 (22) , 5205-5210. https://doi.org/10.1002/ange.201006712
    85. Stéphane Quideau, Céline Douat‐Casassus, Daniela Melanie Delannoy López, Carmelo Di Primo, Stefan Chassaing, Rémi Jacquet, Frédéric Saltel, Elisabeth Genot. Binding of Filamentous Actin and Winding into Fibrillar Aggregates by the Polyphenolic C‐Glucosidic Ellagitannin Vescalagin. Angewandte Chemie International Edition 2011, 50 (22) , 5099-5104. https://doi.org/10.1002/anie.201006712
    86. Arun K. Ghosh, Zachary L. Dawson, Deuk Kyu Moon, Ruoli Bai, Ernest Hamel. Synthesis and biological evaluation of new jasplakinolide (jaspamide) analogs. Bioorganic & Medicinal Chemistry Letters 2010, 20 (17) , 5104-5107. https://doi.org/10.1016/j.bmcl.2010.07.023
    87. Wenhua Li, Andreas Schlecker, Dawei Ma. Total synthesis of antimicrobial and antitumor cyclic depsipeptides. Chemical Communications 2010, 46 (30) , 5403. https://doi.org/10.1039/c0cc00629g
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