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1

Statsuk, Alexander V., Dong Liu, and Sergey A. Kozmin. "Synthesis of Bistramide A." Journal of the American Chemical Society 126, no. 31 (August 2004): 9546–47. http://dx.doi.org/10.1021/ja046588h.

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2

Biard, J. F., C. Grivois, J. F. Verbist, C. Debitus, and J. B. Carre. "Origin of bistramide a identified in Lissoclinum bistratum (Urochordata): possible involvement of symbiotic Prochlorophyta." Journal of the Marine Biological Association of the United Kingdom 70, no. 4 (November 1990): 741–46. http://dx.doi.org/10.1017/s0025315400059014.

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An attempt was made to determine whether bistramide A (=bistratene A), a polycycloether with biological activity isolated from Lissodinum bistratum Sluiter, originates from the ascidian itself or from its symbiont Prochlorophyta. A high-pressure liquid chromatography assay carried out on the whole ascidian, the ascidian without a portion of its Prochloron and the Prochloron themselves gave concentrations respectively of 0.182,0.166 and 0.850%. In view of these results, as well as of the capacity of Prochloron to synthesize complex nitrogenous products and the cytotoxicity of these products, it is hypothesized that bistramide A originates exclusively in Prochloron.
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3

Lowe, Jason T., Iwona E. Wrona, and James S. Panek. "Total Synthesis of Bistramide A." Organic Letters 9, no. 2 (January 2007): 327–30. http://dx.doi.org/10.1021/ol062957y.

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4

Padhi, Birakishore, D. Srinivas Reddy, and Debendra K. Mohapatra. "Gold-catalyzed diastereoselective synthesis of 2,6-trans-disubstituted tetrahydropyran derivatives: application for the synthesis of the C1–C13 fragment of bistramide A and B." RSC Advances 5, no. 117 (2015): 96758–68. http://dx.doi.org/10.1039/c5ra17646h.

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An efficient Au(iii)-catalyzed diastereoselective allylation leading to 2,6-trans-disubstituted tetrahydropyrans and application for the synthesis of the C1–C13 fragment of bistramide A and B is described.
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5

Crimmins, Michael T., and Amy C. DeBaillie. "Enantioselective Total Synthesis of Bistramide A." Journal of the American Chemical Society 128, no. 15 (April 2006): 4936–37. http://dx.doi.org/10.1021/ja057686l.

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6

Yadav, J. S., and Lakshindra Chetia. "Stereoselective Total Synthesis of Bistramide A." Organic Letters 9, no. 22 (October 2007): 4587–89. http://dx.doi.org/10.1021/ol702095n.

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7

Solladié, Guy, Claude Bauder, and Jean-François Biard. "Hemisynthesis of bistramide D by stereoselective reduction of bistramide A. Partial determination of relative and absolute configurations." Tetrahedron Letters 41, no. 40 (September 2000): 7747–50. http://dx.doi.org/10.1016/s0040-4039(00)01323-x.

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8

Bates, Roderick W., and Kalpana Palani. "Model studies towards the bistramide D tetrahydropyran." Tetrahedron Letters 49, no. 17 (April 2008): 2832–34. http://dx.doi.org/10.1016/j.tetlet.2008.02.123.

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9

Bauder, Claude. "Toward an Asymmetric Synthesis of Bistramide K." European Journal of Organic Chemistry 2018, no. 35 (August 24, 2018): 4874–99. http://dx.doi.org/10.1002/ejoc.201800875.

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10

Wipf, Peter, and Tamara D. Hopkins. "Total synthesis and structure validation of (+)-bistramide C." Chemical Communications, no. 27 (2005): 3421. http://dx.doi.org/10.1039/b505100b.

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11

Bates, Roderick W., Lu Li, Kalpana Palani, Wanida Phetsang, and Joanna Kejun Loh. "Synthesis of the Tetrahydropyran Fragment of Bistramide D." Asian Journal of Organic Chemistry 3, no. 7 (May 14, 2014): 792–96. http://dx.doi.org/10.1002/ajoc.201402052.

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12

Bauder, Claude, Jean-Fran?ois Biard, and Guy Solladi? "Synthesis of derivatives of potent antitumor bistramides D and A leading to the first crystal structure of natural bistramide D." Organic & Biomolecular Chemistry 4, no. 10 (2006): 1860. http://dx.doi.org/10.1039/b603767d.

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13

Statsuk, Alexander V., Ruoli Bai, Jeremy L. Baryza, Vishal A. Verma, Ernest Hamel, Paul A. Wender, and Sergey A. Kozmin. "Actin is the primary cellular receptor of bistramide A." Nature Chemical Biology 1, no. 7 (November 13, 2005): 383–88. http://dx.doi.org/10.1038/nchembio748.

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14

Hiebel, Marie-Aude, Béatrice Pelotier, and Olivier Piva. "Stereoselective synthesis of the C1–C13 fragment of bistramide A." Tetrahedron Letters 51, no. 38 (September 2010): 5091–93. http://dx.doi.org/10.1016/j.tetlet.2010.07.119.

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15

Gueyrard, David, Peter Goekjian, Loic Tomas, Thibault Bechet, and Erwann Jeanneau. "Efficient Synthesis of the C1-C13 Fragment of Bistramide A." Synlett 2012, no. 02 (December 9, 2011): 215–18. http://dx.doi.org/10.1055/s-0031-1290097.

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16

Hanna, Ramsey D., Yuta Naro, Alexander Deiters, and Paul E. Floreancig. "Potent and Readily Accessible Bistramide A Analogues through Diverted Total Synthesis." Chemistry - A European Journal 24, no. 61 (October 9, 2018): 16271–75. http://dx.doi.org/10.1002/chem.201804417.

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17

Rizvi, Syed Alipayam, Valentina Tereshko, Anthony A. Kossiakoff, and Sergey A. Kozmin. "Structure of Bistramide A−Actin Complex at a 1.35 Å Resolution." Journal of the American Chemical Society 128, no. 12 (March 2006): 3882–83. http://dx.doi.org/10.1021/ja058319c.

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18

Tomas, Loïc, David Gueyrard, and Peter G. Goekjian. "Synthesis of the spiroketal fragment of bistramide A via an exocyclic enol ether." Tetrahedron Letters 51, no. 35 (September 2010): 4599–601. http://dx.doi.org/10.1016/j.tetlet.2010.06.006.

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19

Bauder, Claude. "Asymmetric Synthesis of the C1-C13 Fragment of the Marine Metabolite Bistramide K." European Journal of Organic Chemistry 2010, no. 32 (September 22, 2010): 6207–16. http://dx.doi.org/10.1002/ejoc.201000881.

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20

Sauviat, M. P., J. M. Chesnais, J. Diacono, J. F. Biard, and J. F. Verbist. "Influence of bistramide A on the twitch tension in rat atrial heart muscle." Experientia 50, no. 10 (October 1994): 926–30. http://dx.doi.org/10.1007/bf01923480.

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21

Gallagher, Paul O., Christopher S. P. McErlean, Mark F. Jacobs, Dianne J. Watters, and William Kitching. "Sub-structure syntheses and relative stereochemistry in the bistramide (bistratene) series of marine metabolites." Tetrahedron Letters 43, no. 3 (January 2002): 531–35. http://dx.doi.org/10.1016/s0040-4039(01)02219-5.

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22

Rizvi, Syed Alipayam, Song Liu, Zhonglei Chen, Colleen Skau, Matthew Pytynia, David R. Kovar, Steven J. Chmura, and Sergey A. Kozmin. "Rationally Simplified Bistramide Analog Reversibly Targets Actin Polymerization and Inhibits Cancer Progressionin Vitroandin Vivo." Journal of the American Chemical Society 132, no. 21 (June 2, 2010): 7288–90. http://dx.doi.org/10.1021/ja101811x.

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23

Pelotier, Béatrice, Olivier Piva, Marie-Aude Hiebel, and Paul Lhoste. "Synthesis of Bistramide A and Analogues, Part 1: Stereoselective Access to Normethyl Tetrahydropyran Subunit." Synlett 2008, no. 8 (May 2008): 1202–4. http://dx.doi.org/10.1055/s-2008-1072714.

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24

Sauviat, Martin-Pierre, Danièle Gouiffes-Barbin, Eudes Ecault, and Jean-Francois Verbist. "Blockade of sodium channels by bistramide A in voltage-clamped frog skeletal muscle fibres." Biochimica et Biophysica Acta (BBA) - Biomembranes 1103, no. 1 (January 1992): 109–14. http://dx.doi.org/10.1016/0005-2736(92)90063-r.

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25

Gueyrard, David. "Extension of the Modified Julia Olefination on Carboxylic Acid Derivatives: Scope and Applications." Synlett 29, no. 01 (October 16, 2017): 34–45. http://dx.doi.org/10.1055/s-0036-1590916.

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This account relates our work in the field of modified Julia olefination to extend this very useful olefination method to carboxylic acid derivatives. Since our preliminary results on lactones in 2005, the reaction has been extended to a large range of derivatives (lactams, imides and anhydrides) through an intra- or intermolecular process leading to a great variety of structures (enol ethers, enamides and exo enol esters). This article will also focus on the application of this methodology for the preparation of biologically interesting compounds and/or total syntheses of natural products such as C-disaccharide, bistramide A, jaspine B and maculalactone B.1 Introduction2 Modified Julia Olefination on Lactones2.1 Methylene Enol Ether Synthesis2.2 Substituted Enol Ether Synthesis2.3 Monofluorinated Enol Ether Synthesis2.4 Difluorinated Enol Ether Synthesis3 Applications3.1 Spiroketal Synthesis3.2 Spirocompound Synthesis3.3 Pseudodisaccharide Synthesis3.4 Total Synthesis of Jaspine B4 Modified Julia Olefination on Other Carboxylic Acid Derivatives4.1 Lactam Olefination and Spiroaminal Synthesis4.2 Bicyclic Enamide Synthesis by Intramolecular Modified Julia Olefination on Imides4.3 Modified Julia Olefination on Anhydrides5 Conclusion
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26

Han, Xun, and Paul E. Floreancig. "Spiroacetal Formation through Telescoped Cycloaddition and Carbon-Hydrogen Bond Functionalization: Total Synthesis of Bistramide A." Angewandte Chemie 126, no. 41 (September 1, 2014): 11255–58. http://dx.doi.org/10.1002/ange.201406819.

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27

Han, Xun, and Paul E. Floreancig. "Spiroacetal Formation through Telescoped Cycloaddition and Carbon-Hydrogen Bond Functionalization: Total Synthesis of Bistramide A." Angewandte Chemie International Edition 53, no. 41 (September 4, 2014): 11075–78. http://dx.doi.org/10.1002/anie.201406819.

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28

Gouiffes, D., M. Juge, N. Grimaud, L. Welin, M. P. Sauviat, Y. Barbin, D. Laurent, C. Roussakis, J. P. Henichart, and J. F. Verbist. "Bistramide A, a new toxin from the urochordata Lissoclinum bistratum Sluiter: Isolation and preliminary characterization." Toxicon 26, no. 12 (January 1988): 1129–36. http://dx.doi.org/10.1016/0041-0101(88)90297-8.

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29

Gouiffès, D., S. Moreau, N. Helbecque, J. L. Bernier, J. P. Hénichart, Y. Barbin, D. Laurent, and J. F. Verbist. "Proton Nuclear Magnetic Study of Bistramide A, a new cytotoxic drug isolated from Lissoclinum Bistratum Sluiter." Tetrahedron 44, no. 2 (January 1988): 451–59. http://dx.doi.org/10.1016/s0040-4020(01)85836-1.

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30

Wipf, Peter, Yoshikazu Uto, and Seiji Yoshimura. "Total Synthesis of a Stereoisomer of Bistramide C and Assignment of Configuration of the Natural Product." Chemistry - A European Journal 8, no. 7 (April 2, 2002): 1670–81. http://dx.doi.org/10.1002/1521-3765(20020402)8:7<1670::aid-chem1670>3.0.co;2-4.

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31

Rizvi, S. A., D. S. Courson, V. A. Keller, R. S. Rock, and S. A. Kozmin. "The dual mode of action of bistramide A entails severing of filamentous actin and covalent protein modification." Proceedings of the National Academy of Sciences 105, no. 11 (March 11, 2008): 4088–92. http://dx.doi.org/10.1073/pnas.0710727105.

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32

Han, Xun, and Paul E. Floreancig. "ChemInform Abstract: Spiroacetal Formation Through Telescoped Cycloaddition and Carbon-Hydrogen Bond Functionalization: Total Synthesis of Bistramide A." ChemInform 46, no. 14 (March 19, 2015): no. http://dx.doi.org/10.1002/chin.201514272.

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33

Sauviat, M.-P., J. M. Chesnais, N. Choukri, J. Diacono, J. F. Biard, and J. F. Verbist. "The polyether Bistramide A affects the calcium sensitivity of the contractile proteins in frog atrial heart muscle." Cell Calcium 14, no. 4 (April 1993): 301–9. http://dx.doi.org/10.1016/0143-4160(93)90051-7.

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34

Lowe, Jason T., and James S. Panek. "Synthesis and [4 + 2]-Annulation of Enantioenriched (Z)-Crotylsilanes: Preparation of the C1−C13 Fragment of Bistramide A." Organic Letters 7, no. 15 (July 2005): 3231–34. http://dx.doi.org/10.1021/ol050982i.

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35

Zuber, Gérard, Michael-Rock Goldsmith, Tamara D. Hopkins, David N. Beratan, and Peter Wipf. "Systematic Assignment of the Configuration of Flexible Natural Products by Spectroscopic and Computational Methods: The Bistramide C Analysis." Organic Letters 7, no. 23 (November 2005): 5269–72. http://dx.doi.org/10.1021/ol052154v.

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36

Tomas, Loïc, Gustav Boije af Gennäs, Marie Aude Hiebel, Peter Hampson, David Gueyrard, Béatrice Pelotier, Jari Yli-Kauhaluoma, Olivier Piva, Janet M. Lord, and Peter G. Goekjian. "Total Synthesis of Bistramide A and Its 36(Z) Isomers: Differential Effect on Cell Division, Differentiation, and Apoptosis." Chemistry - A European Journal 18, no. 24 (April 26, 2012): 7452–66. http://dx.doi.org/10.1002/chem.201102462.

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37

Wipf, Peter, Yoshikazu Uto, and Seiji Yoshimura. "ChemInform Abstract: Total Synthesis of a Stereoisomer of Bistramide C and Assignment of Configuration of the Natural Product." ChemInform 33, no. 32 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200232235.

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38

Herkommer, Daniel, Sandra Dreisigacker, Galina Sergeev, Florenz Sasse, Holger Gohlke, and Dirk Menche. "Design, Synthesis, and Biological Evaluation of Simplified Side Chain Hybrids of the Potent Actin Binding Polyketides Rhizopodin and Bistramide." ChemMedChem 10, no. 3 (January 29, 2015): 470–89. http://dx.doi.org/10.1002/cmdc.201402508.

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39

Yadav, Jhillu Singh, Eppa Gyanchander, Anand Kumar Mishra, Peddapuram Adithya, and Saibal Das. "Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A." Tetrahedron Letters 54, no. 44 (October 2013): 5879–82. http://dx.doi.org/10.1016/j.tetlet.2013.08.085.

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40

Foster, Mark P., Charles L. Mayne, Reinhard Dunkel, Ronald J. Pugmire, David M. Grant, Jean Michel Kornprobst, Jean Francois Verbist, Jean Francois Biard, and Chris M. Ireland. "Revised structure of bistramide A (bistratene A): application of a new program for the automated analysis of 2D INADEQUATE spectra." Journal of the American Chemical Society 114, no. 3 (January 1992): 1110–11. http://dx.doi.org/10.1021/ja00029a062.

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41

Riou, Denis, Christos Roussakis, Nelly Robillard, Jean-François Biard, and Jean-François Verbist. "Bistramide A-induced irreversible arrest of cell proliferation in a non-small-cell bronchopulmonary carcinoma is similar to induction of terminal maturation." Biology of the Cell 77, no. 3 (1993): 261–64. http://dx.doi.org/10.1016/s0248-4900(05)80196-0.

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42

Yadav, Jhillu Singh, Eppa Gyanchander, Anand Kumar Mishra, Peddapuram Adithya, and Saibal Das. "ChemInform Abstract: Novel Iodine Catalyzed Diastereoselective Synthesis of trans-2,6-Disubstituted Tetrahydro-2H-pyrans: Synthesis of C1-C13 Fragment of Bistramide-A." ChemInform 45, no. 10 (February 21, 2014): no. http://dx.doi.org/10.1002/chin.201410150.

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43

Wrona, Iwona E., Jason T. Lowe, Thomas J. Turbyville, Tanya R. Johnson, Julien Beignet, John A. Beutler, and James S. Panek. "Synthesis of a 35-Member Stereoisomer Library of Bistramide A: Evaluation of Effects on actin State, Cell Cycle and Tumor Cell Growth." Journal of Organic Chemistry 74, no. 5 (March 6, 2009): 1897–916. http://dx.doi.org/10.1021/jo802269q.

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44

Padhi, Birakishore, D. Srinivas Reddy, and Debendra K. Mohapatra. "ChemInform Abstract: Gold-Catalyzed Diastereoselective Synthesis of 2,6-trans-Disubstituted Tetrahydropyran Derivatives: Application for the Synthesis of the C1-C13 Fragment of Bistramide A (X) and B (XI)." ChemInform 47, no. 13 (March 2016): no. http://dx.doi.org/10.1002/chin.201613150.

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45

Murphy, Brian T., Shugeng Cao, Peggy Brodie, Jean Maharavo, Hanta Andriamanantoanina, Pierre Ravelonandro, and David G. I. Kingston. "Antiproliferative Bistramides fromTrididemnum cyclopsfrom Madagascar(1)." Journal of Natural Products 72, no. 7 (July 24, 2009): 1338–40. http://dx.doi.org/10.1021/np900072k.

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46

Commandeur, Malgorzata, Claude Commandeur, and Janine Cossy. "Synthesis of a Platform To Access Bistramides and Their Analogues." Organic Letters 13, no. 22 (November 18, 2011): 6018–21. http://dx.doi.org/10.1021/ol202483u.

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47

Biard, Jean-François, Christos Roussakis, Jean-Michel Kornprobst, Danielle Gouiffes-Barbin, Jean-François Verbist, Philippe Cotelle, Mark P. Foster, Chris M. Ireland, and Cécile Debitus. "Bistramides A, B, C, D, and K: A New Class of Bioactive Cyclic Polyethers from Lissoclinum bistratum." Journal of Natural Products 57, no. 10 (October 1994): 1336–45. http://dx.doi.org/10.1021/np50112a002.

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48

Romea, Pedro, Fèlix Urpí, Erik Gálvez, and Ricard Parelló. "Stereoselective Addition of Titanium Enolates to Functionalized Acetals: A Novel Approach to the γ-Amino Acid of Bistramides and FR252921." Synlett 2008, no. 19 (November 12, 2008): 2951–54. http://dx.doi.org/10.1055/s-0028-1087351.

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49

Statsuk, Alexander V., Dong Liu, and Sergey A. Kozmin. "Synthesis of Bistramide A." ChemInform 35, no. 49 (December 7, 2004). http://dx.doi.org/10.1002/chin.200449212.

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50

"Synthesis of Bistramide A." Synfacts 2007, no. 06 (May 22, 2007): 0569. http://dx.doi.org/10.1055/s-2007-968509.

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