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Synthetic Transformations of Eleutherobin Reveal New Features of Its Microtubule-Stabilizing Pharmacophore

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Departments of Chemistry and EOS University of British Columbia Vancouver, British Columbia, Canada, V6T 1Z1 Department of Biochemistry and Molecular Biology University of British Columbia Vancouver, British Columbia, Canada, V6T 1Z3
Cite this: J. Am. Chem. Soc. 2001, 123, 35, 8632–8633
Publication Date (Web):August 10, 2001
https://doi.org/10.1021/ja016459q
Copyright © 2001 American Chemical Society

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     Departments of Chemistry and EOS.

     Department of Biochemistry and Molecular Biology.

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    Experimental procedures for the synthetic transformations and tabulated bioactivity data (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

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    12. S.Y. Frankie Mak, Gary C.H. Chiang, James E.P. Davidson, John E. Davies, Andrew Ayscough, Gilles Pain, Jonathan W. Burton, Andrew B. Holmes. Synthesis of simplified analogues of eleutherobin via a Claisen rearrangement/RCM strategy. Tetrahedron: Asymmetry 2009, 20 (6-8) , 921-944. https://doi.org/10.1016/j.tetasy.2009.03.010
    13. Celso Sandoval, Jose L. López-Pérez, Francisco Bermejo. Synthesis of a 10-membered ring with eleutheside functionality by Nozaki–Hiyama–Kishi coupling. Tetrahedron 2007, 63 (47) , 11738-11747. https://doi.org/10.1016/j.tet.2007.08.099
    14. Karl-Heinz Altmann, Jürg Gertsch. Anticancer drugs from nature—natural products as a unique source of new microtubule-stabilizing agents. Nat. Prod. Rep. 2007, 24 (2) , 327-357. https://doi.org/10.1039/B515619J
    15. Damiano Castoldi, Lorenzo Caggiano, Laura Panigada, Ofer Sharon, Anna M. Costa, Cesare Gennari. A Formal Total Synthesis of Eleutherobin Using the Ring‐Closing Metathesis (RCM) Reaction of a Densely Functionalized Diene as the Key Step: Investigation of the Unusual Kinetically Controlled RCM Stereochemistry. Chemistry – A European Journal 2006, 12 (1) , 51-62. https://doi.org/10.1002/chem.200500749
    16. John Q Trojanowski, Amos B Smith, Donna Huryn, Virginia M-Y Lee. Microtubule-stabilising drugs for therapy of Alzheimer’s disease and other neurodegenerative disorders with axonal transport impairments. Expert Opinion on Pharmacotherapy 2005, 6 (5) , 683-686. https://doi.org/10.1517/14656566.6.5.683
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    19. Damiano Castoldi, Lorenzo Caggiano, Laura Panigada, Ofer Sharon, Anna M. Costa, Cesare Gennari. A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring‐Closing‐Metathesis Reaction of a Densely Functionalized Diene. Angewandte Chemie 2005, 117 (4) , 594-597. https://doi.org/10.1002/ange.200461767
    20. Damiano Castoldi, Lorenzo Caggiano, Laura Panigada, Ofer Sharon, Anna M. Costa, Cesare Gennari. A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring‐Closing‐Metathesis Reaction of a Densely Functionalized Diene. Angewandte Chemie International Edition 2005, 44 (4) , 588-591. https://doi.org/10.1002/anie.200461767
    21. V.M. Dembitsky, H. Abu Ali, M. Srebnik. Synthesis of selected biologically active compounds via allylboration. 2005, 299-336. https://doi.org/10.1016/S0169-3158(06)80005-8
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    23. S Chandrasekhar, V Jagadeshwar, Ch Narsihmulu, M Sarangapani, D.R Krishna, J Vidyasagar, Dolly Vijay, G.Narahari Sastry. Design, synthesis and cytotoxic studies on the simplified oxy analog of eleutherobin. Bioorganic & Medicinal Chemistry Letters 2004, 14 (14) , 3687-3689. https://doi.org/10.1016/j.bmcl.2004.05.017
    24. Raphael Beumer, Pau Bayón, Piergiuliano Bugada, Sylvie Ducki, Nicola Mongelli, Federico Riccardi Sirtori, Joachim Telser, Cesare Gennari. Synthesis of novel simplified sarcodictyin/eleutherobin analogs with potent microtubule-stabilizing activity, using ring closing metathesis as the key-step. Tetrahedron 2003, 59 (44) , 8803-8820. https://doi.org/10.1016/j.tet.2003.08.057
    25. Orazio Taglialatela‐Scafati, Kyle S. Craig, Delphine Rebérioux, Michel Roberge, Raymond J. Andersen. Briarane, Erythrane, and Aquariane Diterpenoids from the Caribbean Gorgonian Erythropodium caribaeorum. European Journal of Organic Chemistry 2003, 2003 (18) , 3515-3523. https://doi.org/10.1002/ejoc.200300214
    26. Ulf Diederichsen. Eleutherobin: Synthesis, Structure/Activity Relationship, and Pharmacophore. 2003, 317-325. https://doi.org/10.1002/9783527619986.ch29
    27. Ulf Diederichsen. Eleutherobin: Synthesis, Structure/Activity Relationship, and Pharmacophore. 2003, 317-325. https://doi.org/10.1002/9783527620784.ch29d
    28. Raphael Beumer, Pau Bayón, Piergiuliano Bugada, Sylvie Ducki, Nicola Mongelli, Federico Riccardi Sirtori, Joachim Telser, Cesare Gennari. Synthesis of novel simplified eleutheside analogues with potent microtubule-stabilizing activity, using ring-closing metathesis as the key-step. Tetrahedron Letters 2003, 44 (4) , 681-684. https://doi.org/10.1016/S0040-4039(02)02646-1
    29. Celso Sandoval, Elena Redero, Miguel A. Mateos-Timoneda, Francisco A. Bermejo. Suitable entry to a 10-membered ring with eleutheside functionality through Nozaki–Hiyama condensation. Tetrahedron Letters 2002, 43 (37) , 6521-6524. https://doi.org/10.1016/S0040-4039(02)01475-2
    30. Joachim Telser, Raphael Beumer, Andrew A Bell, Simona M Ceccarelli, Diego Monti, Cesare Gennari. Synthesis of a simplified sarcodictyin analogue which retains microtubule stabilising properties. Tetrahedron Letters 2001, 42 (52) , 9187-9190. https://doi.org/10.1016/S0040-4039(01)02045-7
    31. Guangyi Wang, Weiping Tang, Robert R. Bidigare. Terpenoids As Therapeutic Drugs and Pharmaceutical Agents. , 197-227. https://doi.org/10.1007/978-1-59259-976-9_9

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