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Total Synthesis of (R)-Telomestatin

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Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, The University of Tokyo, Institute of Molecular and Cellular Biosciences, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan, and National Institute of Advanced Industrial Science and Technology (AIST), Biological Information Research Center (BIRC), Protein Network Team, Low M.W. Chemical Laboratory, AIST Tokyo Waterfront Bio-IT Research Building, 2-42 Aomi, Koto-ku, Tokyo 135-0064, Japan
Cite this: Org. Lett. 2006, 8, 18, 4165–4167
Publication Date (Web):August 9, 2006
https://doi.org/10.1021/ol061793i
Copyright © 2006 American Chemical Society
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    Abstract

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    We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-tBu) moiety using Kelly's method (PPh3(O)−Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.

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    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    †

     Tokyo Institute of Technology.

    §

     The University of Tokyo.

    ‡

     National Institute of Advanced Industrial Science and Technology.

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    Experimental details, NMR spectra of 12−16, and NMR, UV, and CD spectra of 1. This material is available free of charge via the Internet at http://pubs.acs.org.

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    33. Sefan Asamitsu, Yue Li, Toshikazu Bando, Hiroshi Sugiyama. Ligand‐Mediated G‐Quadruplex Induction in a Double‐Stranded DNA Context by Cyclic Imidazole/Lysine Polyamide. ChemBioChem 2016, 17 (14) , 1317-1322. https://doi.org/10.1002/cbic.201600198
    34. Martin S. Seyfried, Jawad Alzeer, Nathan W. Luedtke. Molecular Design and Synthesis of a Planar Telomestatin Analogue. European Journal of Organic Chemistry 2016, 2016 (2) , 367-372. https://doi.org/10.1002/ejoc.201501103
    35. John A. Joule. Natural Products Containing Nitrogen Heterocycles—Some Highlights 1990–2015. 2016, 81-106. https://doi.org/10.1016/bs.aihch.2015.10.005
    36. Zoe J. Anderson, David J. Fox. Total synthesis of the azolemycins. Organic & Biomolecular Chemistry 2016, 14 (4) , 1450-1454. https://doi.org/10.1039/C5OB02520F
    37. Bohdan A. Chalyk, Inna Y. Kandaurova, Kateryna V. Hrebeniuk, Olga V. Manoilenko, Irene B. Kulik, Rustam T. Iminov, Vladimir Kubyshkin, Anton V. Tverdokhlebov, Osman K. Ablialimov, Pavel K. Mykhailiuk. A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics. RSC Advances 2016, 6 (31) , 25713-25723. https://doi.org/10.1039/C6RA02365G
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    39. Supravat Samanta, Ramachandra Reddy Donthiri, Milan Dinda, Subbarayappa Adimurthy. Iodine catalysed intramolecular C(sp 3 )–H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides. RSC Advances 2015, 5 (82) , 66718-66722. https://doi.org/10.1039/C5RA13441B
    40. Masahito Yoshida. Total Synthesis of Biologically Active Natural Products toward Elucidation of the Mode of Action. YAKUGAKU ZASSHI 2015, 135 (10) , 1099-1108. https://doi.org/10.1248/yakushi.15-00184
    41. Takayuki Doi, Masahito Yoshida, Kazuaki Shibata. Total Synthesis of Telomestatin and its Analogues. Journal of Synthetic Organic Chemistry, Japan 2015, 73 (1) , 3-13. https://doi.org/10.5059/yukigoseikyokaishi.73.3
    42. Ivan Romero‐Estudillo, Venkateswara Rao Batchu, Alicia Boto. One‐Pot Conversion of Amino Acids into 2,5‐Disubstituted Oxazoles: No Metals Needed. Advanced Synthesis & Catalysis 2014, 356 (18) , 3742-3748. https://doi.org/10.1002/adsc.201400496
    43. N. S. Ilyinsky, A. M. Varizhuk, A. D. Beniaminov, M. A. Puzanov, A. K. Shchyolkina, D. N. Kaluzhny. G-quadruplex ligands: Mechanisms of anticancer action and target binding. Molecular Biology 2014, 48 (6) , 778-794. https://doi.org/10.1134/S0026893314060077
    44. Sebastian Müller, Raphaël Rodriguez. G-quadruplex interacting small molecules and drugs: from bench toward bedside. Expert Review of Clinical Pharmacology 2014, 7 (5) , 663-679. https://doi.org/10.1586/17512433.2014.945909
    45. Fuling Qi, Lianxun Gao, Fushe Han. Design and synthesis of macrocyclic polyoxazoles. Chemical Research in Chinese Universities 2014, 30 (4) , 587-592. https://doi.org/10.1007/s40242-014-4069-z
    46. Asfa Ali, Santanu Bhattacharya. DNA binders in clinical trials and chemotherapy. Bioorganic & Medicinal Chemistry 2014, 22 (16) , 4506-4521. https://doi.org/10.1016/j.bmc.2014.05.030
    47. Fuling Qi, Lianxun Gao, Fushe Han. Design and Synthesis of Polyoxazole‐based Macrocycles Tethered with a Phosphonate Group. Chinese Journal of Chemistry 2014, 32 (7) , 585-591. https://doi.org/10.1002/cjoc.201400213
    48. Stephan A. Ohnmacht, Stephen Neidle. Small-molecule quadruplex-targeted drug discovery. Bioorganic & Medicinal Chemistry Letters 2014, 24 (12) , 2602-2612. https://doi.org/10.1016/j.bmcl.2014.04.029
    49. Estela Haldón, Maria Besora, Israel Cano, Xacobe C. Cambeiro, Miquel A. Pericàs, Feliu Maseras, M. Carmen Nicasio, Pedro J. Pérez. Reaction of Alkynes and Azides: Not Triazoles Through Copper–Acetylides but Oxazoles Through Copper–Nitrene Intermediates. Chemistry – A European Journal 2014, 20 (12) , 3463-3474. https://doi.org/10.1002/chem.201303737
    50. Basudeb Maji, Santanu Bhattacharya. Advances in the molecular design of potential anticancer agents via targeting of human telomeric DNA. Chem. Commun. 2014, 50 (49) , 6422-6438. https://doi.org/10.1039/C4CC00611A
    51. Philjun Kang, Kyu Myung Lee, Won Koo Lee, Kyu Hyung Lee, Byeongno Lee, Jaeheung Cho, Nam Hwi Hur. One-pot solvent-free reductive amination with a solid ammonium carbamate salt from CO 2 and amine. RSC Adv. 2014, 4 (86) , 46203-46207. https://doi.org/10.1039/C4RA07558G
    52. Kazuaki Shibata, Masahito Yoshida, Takashi Takahashi, Motoki Takagi, Kazuo Shin-ya, Takayuki Doi. Synthesis of Heptaoxazole Macrocyclic Analogues of Telomestatin and Evaluation of Their Telomerase Inhibitory Activities. Bulletin of the Chemical Society of Japan 2013, 86 (12) , 1453-1465. https://doi.org/10.1246/bcsj.20130198
    53. Keisuke Iida, Kazuo Nagasawa. Macrocyclic Polyoxazoles as G ‐Quadruplex Ligands. The Chemical Record 2013, 13 (6) , 539-548. https://doi.org/10.1002/tcr.201300015
    54. Maria Ruden, Neelu Puri. Novel anticancer therapeutics targeting telomerase. Cancer Treatment Reviews 2013, 39 (5) , 444-456. https://doi.org/10.1016/j.ctrv.2012.06.007
    55. Hiroshi Shinokubo, Koichiro Oshima, Zhenhua Gu, Armen Zakarian. Bromotrichloromethane. 2012https://doi.org/10.1002/047084289X.rn00250.pub2
    56. Chung-Mao Pan, Chun-Chieh Lin, Seong Jong Kim, Robert P. Sellers, Shelli R. McAlpine. Progress toward the synthesis of Urukthapelstatin A and two analogues. Tetrahedron Letters 2012, 53 (32) , 4065-4069. https://doi.org/10.1016/j.tetlet.2012.05.105
    57. Renzo Rossi, Fabio Bellina, Marco Lessi. Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes. Advanced Synthesis & Catalysis 2012, 354 (7) , 1181-1255. https://doi.org/10.1002/adsc.201100942
    58. Liangfeng Fu. Metalation of Oxazoles and Benzoxazoles. 2012, 103-154. https://doi.org/10.1007/7081_2012_81
    59. Stephen Neidle. Telomeric Quadruplex Ligands II. 2012, 93-107. https://doi.org/10.1016/B978-0-12-375138-6.00005-4
    60. Dougal J. Ritson, John E. Moses. A fragment based click chemistry approach towards hybrid G-quadruplex ligands: design, synthesis and biophysical evaluation. Tetrahedron 2012, 68 (1) , 197-203. https://doi.org/10.1016/j.tet.2011.10.066
    61. Kazuo Nagasawa, Keisuke Iida, Satoki Majima, Terumi Ohtake, Masayuki Tera, Kazuo Shin-ya. Design and Synthesis of G-Quadruplex Ligands Bearing Macrocyclic Hexaoxazoles with Four-Way Side Chains. HETEROCYCLES 2012, 84 (1) , 401. https://doi.org/10.3987/COM-11-S(P)88
    62. Brian M. Stoltz, Daniel D. Caspi, Haiming Zhang, Scott C. Virgil, Fabian M. Piller. Rapid and Convergent Synthesis of a 2,4’-Linked Tri-oxazole in an Approach to Poly-oxazoles. HETEROCYCLES 2012, 86 (2) , 1003. https://doi.org/10.3987/COM-12-S(N)118
    63. Christian Spiteri, Dougal J. Ritson, Amani Awaad, John E. Moses. Silver mediated one-step synthesis of oxazoles from α-haloketones. Journal of Saudi Chemical Society 2011, 15 (4) , 375-378. https://doi.org/10.1016/j.jscs.2011.06.021
    64. Florian Hamon, Eric Largy, Aurore Guédin‐Beaurepaire, Myriam Rouchon‐Dagois, Assitan Sidibe, David Monchaud, Jean‐Louis Mergny, Jean‐Francois Riou, Chi‐Hung Nguyen, Marie‐Paule Teulade‐Fichou. An Acyclic Oligoheteroaryle That Discriminates Strongly between Diverse G‐Quadruplex Topologies. Angewandte Chemie 2011, 123 (37) , 8904-8908. https://doi.org/10.1002/ange.201103422
    65. Florian Hamon, Eric Largy, Aurore Guédin‐Beaurepaire, Myriam Rouchon‐Dagois, Assitan Sidibe, David Monchaud, Jean‐Louis Mergny, Jean‐Francois Riou, Chi‐Hung Nguyen, Marie‐Paule Teulade‐Fichou. An Acyclic Oligoheteroaryle That Discriminates Strongly between Diverse G‐Quadruplex Topologies. Angewandte Chemie International Edition 2011, 50 (37) , 8745-8749. https://doi.org/10.1002/anie.201103422
    66. David W. Knight. Oxazole and Its Derivatives. 2011, 403-458. https://doi.org/10.1002/9783527634880.ch12
    67. Zhengshuang Xu, Tao Ye. Thiazoline and Thiazole and their Derivatives. 2011, 459-505. https://doi.org/10.1002/9783527634880.ch13
    68. Siti Mariam Mohd Nor, Zhengshuang Xu, Tao Ye. Bioactive Macrocyclic Natural Products. 2011, 569-619. https://doi.org/10.1002/9783527634880.ch16
    69. Alan E. Bilsland, Claire J. Cairney, W. Nicol Keith. Targeting the telomere and shelterin complex for cancer therapy: current views and future perspectives. Journal of Cellular and Molecular Medicine 2011, 15 (2) , 179-186. https://doi.org/10.1111/j.1582-4934.2010.01253.x
    70. Takayuki Doi, Kazuaki Shibata, Masahito Yoshida, Motoki Takagi, Masayuki Tera, Kazuo Nagasawa, Kazuo Shin-ya, Takashi Takahashi. (S)-Stereoisomer of telomestatin as a potent G-quadruplex binder and telomerase inhibitor. Org. Biomol. Chem. 2011, 9 (2) , 387-393. https://doi.org/10.1039/C0OB00513D
    71. Jack Li-Yang Chen, Jonathan Sperry, Nancy Y. Ip, Margaret A. Brimble. Natural products targeting telomere maintenance. MedChemComm 2011, 2 (4) , 229. https://doi.org/10.1039/c0md00241k
    72. Masayuki Tera, Keisuke Iida, Kazuo Shin-ya, Kazuo Nagasawa. Development of Macrocyclic Polyoxazoles and Evaluation of Their G-Quadruplex Stabilizing Activities. Journal of Synthetic Organic Chemistry, Japan 2011, 69 (2) , 129-139. https://doi.org/10.5059/yukigoseikyokaishi.69.129
    73. Aurèle Piazza, Jean-Baptiste Boulé, Judith Lopes, Katie Mingo, Eric Largy, Marie-Paule Teulade-Fichou, Alain Nicolas. Genetic instability triggered by G-quadruplex interacting Phen-DC compounds in Saccharomyces cerevisiae. Nucleic Acids Research 2010, 38 (13) , 4337-4348. https://doi.org/10.1093/nar/gkq136
    74. Kazuaki Shibata, Masahito Yoshida, Takayuki Doi, Takashi Takahashi. Derivatization of a tris-oxazole using Pd-catalyzed coupling reactions of a 5-bromooxazole moiety. Tetrahedron Letters 2010, 51 (13) , 1674-1677. https://doi.org/10.1016/j.tetlet.2010.01.064
    75. Amit Arora, Niti Kumar, Tani Agarwal, Souvik Maiti. Retraction: Human telomeric G‐quadruplex: targeting with small molecules. The FEBS Journal 2010, 277 (5) , 1345-1345. https://doi.org/10.1111/j.1742-4658.2009.07461.x
    76. Masayuki Tera, Keisuke Iida, Kazunori Ikebukuro, Hiroyuki Seimiya, Kazuo Shin-ya, Kazuo Nagasawa. Visualization of G-quadruplexes by using a BODIPY-labeled macrocyclic heptaoxazole. Organic & Biomolecular Chemistry 2010, 8 (12) , 2749. https://doi.org/10.1039/c002117b
    77. Kazuo Nagasawa, Satoki Majima, Masayuki Tera, Keisuke Iida, Kazuo Shin-ya. Design and Synthesis of Telomestatin Derivatives Containing Methyl Oxazole and Their G-Quadruplex Stabilizing Activities. HETEROCYCLES 2010, 82 (2) , 1345. https://doi.org/10.3987/COM-10-S(E)85
    78. Marco A. Ciufolini, Jianmin Zhang, Pierre-Yves Coqueron. Development and Applications of an Oxazole-Forming Reaction. HETEROCYCLES 2010, 82 (2) , 949. https://doi.org/10.3987/REV-10-SR(E)3
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    80. David Monchaud, Anton Granzhan, Nicolas Saettel, Aurore Guédin, Jean-Louis Mergny, Marie-Paule Teulade-Fichou. “ One Ring to Bind Them All ”—Part I: The Efficiency of the Macrocyclic Scaffold for G-Quadruplex DNA Recognition. Journal of Nucleic Acids 2010, 2010 , 1-19. https://doi.org/10.4061/2010/525862
    81. Yuan-Chin Tsai, Haiyan Qi, Chao-Po Lin, Ren-Kuo Lin, John E. Kerrigan, Suzanne G. Rzuczek, Edmond J. LaVoie, Joseph E. Rice, Daniel S. Pilch, Yi Lisa Lyu, Leroy F. Liu. A G-quadruplex Stabilizer Induces M-phase Cell Cycle Arrest. Journal of Biological Chemistry 2009, 284 (34) , 22535-22543. https://doi.org/10.1074/jbc.M109.020230
    82. Marco Franceschin. G‐Quadruplex DNA Structures and Organic Chemistry: More Than One Connection. European Journal of Organic Chemistry 2009, 2009 (14) , 2225-2238. https://doi.org/10.1002/ejoc.200801196
    83. Akira Sakakura, Rei Kondo, Shuhei Umemura, Kazuaki Ishihara. Dehydrative cyclization of serine, threonine, and cysteine residues catalyzed by molybdenum(VI) oxo compounds. Tetrahedron 2009, 65 (10) , 2102-2109. https://doi.org/10.1016/j.tet.2008.12.074
    84. Masayuki Tera, Keisuke Iida, Hiromichi Ishizuka, Motoki Takagi, Masami Suganuma, Takayuki Doi, Kazuo Shin‐ya, Kazuo Nagasawa. Synthesis of a Potent G‐Quadruplex‐Binding Macrocyclic Heptaoxazole. ChemBioChem 2009, 10 (3) , 431-435. https://doi.org/10.1002/cbic.200800563
    85. Zhong Jin. Muscarine, imidazole, oxazole and thiazole alkaloids. Natural Product Reports 2009, 26 (3) , 382. https://doi.org/10.1039/b718045b
    86. Keisuke Iida, Masayuki Tera, Takatsugu Hirokawa, Kazuo Shin-ya, Kazuo Nagasawa. G-quadruplex recognition by macrocyclic hexaoxazole (6OTD) dimer: greater selectivity than monomer. Chemical Communications 2009, 29 (42) , 6481. https://doi.org/10.1039/b910242f
    87. Masayuki Tera, Hiromichi Ishizuka, Motoki Takagi, Masami Suganuma, Kazuo Shin‐ya, Kazuo Nagasawa. Macrocyclic Hexaoxazoles as Sequence‐ and Mode‐Selective G‐Quadruplex Binders. Angewandte Chemie 2008, 120 (30) , 5639-5642. https://doi.org/10.1002/ange.200801235
    88. Masayuki Tera, Hiromichi Ishizuka, Motoki Takagi, Masami Suganuma, Kazuo Shin‐ya, Kazuo Nagasawa. Macrocyclic Hexaoxazoles as Sequence‐ and Mode‐Selective G‐Quadruplex Binders. Angewandte Chemie International Edition 2008, 47 (30) , 5557-5560. https://doi.org/10.1002/anie.200801235
    89. M. Christmann. Organocatalytic Syntheses of Bioactive Natural Products. 2008, 51-75. https://doi.org/10.1007/2789_2007_066
    90. Yong-Jin Wu, Bingwei V. Yang. Chapter 5.5 Five-membered ring systems: with N and S (Se) atoms. 2008, 242-276. https://doi.org/10.1016/S0959-6380(08)80011-6
    91. Stefano Cicchi, Franca M. Cordero, Donatella Giomi. Chapter 5.7 Five-membered ring systems with O & N atoms. 2008, 288-313. https://doi.org/10.1016/S0959-6380(08)80013-X
    92. David Monchaud, Marie-Paule Teulade-Fichou. A hitchhiker's guide to G-quadruplex ligands. Org. Biomol. Chem. 2008, 6 (4) , 627-636. https://doi.org/10.1039/B714772B
    93. Jon Deeley, Anna Bertram, Gerald Pattenden. Novel polyoxazole-based cyclopeptides from Streptomyces sp. Total synthesis of the cyclopeptide YM-216391 and synthetic studies towards telomestatin. Organic & Biomolecular Chemistry 2008, 6 (11) , 1994. https://doi.org/10.1039/b802477d
    94. Jörg Linder, Alexander J. Blake, Christopher J. Moody. Total synthesis of siphonazole and its O-methyl derivative, structurally unusual bis-oxazole natural products. Organic & Biomolecular Chemistry 2008, 6 (21) , 3908. https://doi.org/10.1039/b810855b
    95. Rachael A. Hughes, Christopher J. Moody. Von Aminosäuren zu Heteroarenen – Thiopeptid‐Antibiotika als heterocyclische Peptide aus der Natur. Angewandte Chemie 2007, 119 (42) , 8076-8101. https://doi.org/10.1002/ange.200700728
    96. Rachael A. Hughes, Christopher J. Moody. From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides. Angewandte Chemie International Edition 2007, 46 (42) , 7930-7954. https://doi.org/10.1002/anie.200700728
    97. Delia Hernández, Estela Riego, Andrés Francesch, Carmen Cuevas, Fernando Albericio, Mercedes Álvarez. Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization. Tetrahedron 2007, 63 (39) , 9862-9870. https://doi.org/10.1016/j.tet.2007.06.103
    98. Danny Ganame, Tim Quach, Charlotte Poole, Mark A. Rizzacasa. Synthesis of the C9–C29 fragments of ajudazols A and B. Tetrahedron Letters 2007, 48 (33) , 5841-5843. https://doi.org/10.1016/j.tetlet.2007.06.072
    99. Hiroshi Araki, Tadashi Katoh, Munenori Inoue. Iterative two-step strategy for C2–C4′ linked poly-oxazole synthesis using Suzuki–Miyaura cross-coupling reaction. Tetrahedron Letters 2007, 48 (21) , 3713-3717. https://doi.org/10.1016/j.tetlet.2007.03.109
    100. Takayuki Doi, Masahito Yoshida, Kazuo Shin‐ya, Takashi Takahashi. Total Synthesis of (R)‐Telomestatin.. ChemInform 2007, 38 (4) https://doi.org/10.1002/chin.200704204
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