ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Total synthesis of (.+-.)-saxitoxin

Cite this: J. Am. Chem. Soc. 1984, 106, 19, 5594–5598
Publication Date (Print):September 1, 1984
https://doi.org/10.1021/ja00331a032
    ACS Legacy Archive

    Article Views

    1500

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 99 publications.

    1. Yuya Okuyama, Ryosuke Okamoto, Shori Mukai, Kyoko Kinoshita, Takaaki Sato, Noritaka Chida. Synthesis of Saxitoxin and Its Derivatives. Organic Letters 2020, 22 (21) , 8697-8701. https://doi.org/10.1021/acs.orglett.0c03281
    2. Sohei Ueno, Atsuo Nakazaki, and Toshio Nishikawa . A Synthetic Strategy for Saxitoxin Skeleton by a Cascade Bromocyclization: Total Synthesis of (+)-Decarbamoyl-α-saxitoxinol. Organic Letters 2016, 18 (24) , 6368-6371. https://doi.org/10.1021/acs.orglett.6b03262
    3. John V. Mulcahy, James R. Walker, Jeffrey E. Merit, Alan Whitehead, and J. Du Bois . Synthesis of the Paralytic Shellfish Poisons (+)-Gonyautoxin 2, (+)-Gonyautoxin 3, and (+)-11,11-Dihydroxysaxitoxin. Journal of the American Chemical Society 2016, 138 (18) , 5994-6001. https://doi.org/10.1021/jacs.6b02343
    4. Ling Xu, Yu-Chen Wang, Wangyang Ma, Wen-Xiong Zhang, and Zhenfeng Xi . Mechanistic Insights into N—N Bond Cleavage in Catalytic Guanylation Reactions between 1,2-Diarylhydrazines and Carbodiimides. The Journal of Organic Chemistry 2014, 79 (24) , 12004-12009. https://doi.org/10.1021/jo501865b
    5. Takuya Hashimoto, Yuka Takiguchi, and Keiji Maruoka . Catalytic Asymmetric Three-Component 1,3-Dipolar Cycloaddition of Aldehydes, Hydrazides, and Alkynes. Journal of the American Chemical Society 2013, 135 (31) , 11473-11476. https://doi.org/10.1021/ja405444c
    6. William H. Parsons and J. Du Bois . Maleimide Conjugates of Saxitoxin as Covalent Inhibitors of Voltage-Gated Sodium Channels. Journal of the American Chemical Society 2013, 135 (29) , 10582-10585. https://doi.org/10.1021/ja4019644
    7. David A. Schiedler, Jessica K. Vellucci, and Christopher M. Beaudry . Formation of Carbon–Carbon Bonds Using Aminal Radicals. Organic Letters 2012, 14 (23) , 6092-6095. https://doi.org/10.1021/ol3029912
    8. Vasudev R. Bhonde and Ryan E. Looper . A Stereocontrolled Synthesis of (+)-Saxitoxin. Journal of the American Chemical Society 2011, 133 (50) , 20172-20174. https://doi.org/10.1021/ja2098063
    9. Ryan A. Altman, Bradley L. Nilsson, Larry E. Overman, Javier Read de Alaniz, Jason M. Rohde, and Veronique Taupin . Total Synthesis of (+)-Nankakurines A and B and (±)-5-epi-Nankakurine A. The Journal of Organic Chemistry 2010, 75 (22) , 7519-7534. https://doi.org/10.1021/jo101619d
    10. Ken S. Feldman and Paiboon Ngernmeesri. Dragmacidin E Synthesis Studies. Preparation of a Model Heptacyclic Core Structure. Organic Letters 2010, 12 (20) , 4502-4505. https://doi.org/10.1021/ol1018008
    11. Osamu Iwamoto and Kazuo Nagasawa. Total Synthesis of (+)-Decarbamoylsaxitoxin and (+)-Gonyautoxin 3. Organic Letters 2010, 12 (9) , 2150-2153. https://doi.org/10.1021/ol1006696
    12. Philip Magnus, Negar Garizi, Kimberly A. Seibert and Alexandra Ornholt. Synthesis of Carbamates from Diethoxycarbonyl Hydrazine Derivatives by E1cB Eliminative Cleavage of the N−N′-Bond Rather than Reduction. Organic Letters 2009, 11 (24) , 5646-5648. https://doi.org/10.1021/ol902313v
    13. John V. Mulcahy and J. Du Bois. A Stereoselective Synthesis of (+)-Gonyautoxin 3. Journal of the American Chemical Society 2008, 130 (38) , 12630-12631. https://doi.org/10.1021/ja805651g
    14. Bradley L. Nilsson, Larry E. Overman, Javier Read de Alaniz and Jason M. Rohde. Enantioselective Total Syntheses of Nankakurines A and B: Confirmation of Structure and Establishment of Absolute Configuration. Journal of the American Chemical Society 2008, 130 (34) , 11297-11299. https://doi.org/10.1021/ja804624u
    15. William G. O'Neal,, William P. Roberts,, Indranath Ghosh, and, Peter A. Jacobi. Studies in Chlorin Chemistry. II. A Versatile Synthesis of Dihydrodipyrrins. The Journal of Organic Chemistry 2005, 70 (18) , 7243-7251. https://doi.org/10.1021/jo050907l
    16. Alexander L. Ruchelman,, Peter J. Houghton,, Nai Zhou,, Angela Liu,, Leroy F. Liu, and, Edmond J. LaVoie. 5-(2-Aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones:  Variation of N-Alkyl Substituents Modulates Sensitivity to Efflux Transporters Associated with Multidrug Resistance. Journal of Medicinal Chemistry 2005, 48 (3) , 792-804. https://doi.org/10.1021/jm049447z
    17. Anna V. Elleman, J. Du Bois. Chemical and Biological Tools for the Study of Voltage‐Gated Sodium Channels in Electrogenesis and Nociception. ChemBioChem 2022, 23 (13) https://doi.org/10.1002/cbic.202100625
    18. Joana F. Leal, Maria L. S. Cristiano. Marine paralytic shellfish toxins: chemical properties, mode of action, newer analogues, and structure–toxicity relationship. Natural Product Reports 2022, 39 (1) , 33-57. https://doi.org/10.1039/D1NP00009H
    19. Grygoriy Y. Remennikov. Synthesis of pyrimidine-containing alkaloids. 2022, 49-367. https://doi.org/10.1016/bs.alkal.2021.11.001
    20. Kazuo Nagasawa. Total Synthesis of Saxitoxins. Journal of Synthetic Organic Chemistry, Japan 2021, 79 (1) , 43-53. https://doi.org/10.5059/yukigoseikyokaishi.79.43
    21. Uroš Grošelj, Jurij Svete, . [3 + 2] Cycloadditions of Azomethine Imines. 2020, 529-930. https://doi.org/10.1002/0471264180.or103.02
    22. Hayate Ishizuka, Kazuo Nagasawa. Synthesis of Paralytic Shellfish Toxins: Saxitoxins. 2020, 131-152. https://doi.org/10.1007/7081_2020_44
    23. René Pita, Arturo Anadón, Alejandro Romero, Kamil Kuca. Chemical weapons of mass destruction and terrorism: a threat analysis. 2020, 79-94. https://doi.org/10.1016/B978-0-12-819090-6.00007-6
    24. Kanna Adachi, Hayate Ishizuka, Minami Odagi, Kazuo Nagasawa. Synthetic Approaches to Zetekitoxin AB, a Potent Voltage-Gated Sodium Channel Inhibitor. Marine Drugs 2020, 18 (1) , 24. https://doi.org/10.3390/md18010024
    25. Lapo Luconi, Giulia Tuci, Dmitry Yakhvarov, Giovanni Poli, Andrea Rossin, Aliya Khusnuriyalova, Giuliano Giambastiani. Imidazole‐Bridged Tetrameric Group(IV) Heteroleptic Complexes from the Spontaneous Metal‐Ligand Assembly of a Potentially N 4 ‐Tetradentate Ligand. European Journal of Inorganic Chemistry 2019, 2019 (39-40) , 4384-4393. https://doi.org/10.1002/ejic.201900763
    26. Giacomo Mari, Gianfranco Favi, Stefania Santeusanio, Fabio Mantellini, Lucia De Crescentini. A practical and effective method for the N–N bond cleavage of N-amino-heterocycles. Organic Chemistry Frontiers 2019, 6 (19) , 3408-3414. https://doi.org/10.1039/C9QO00895K
    27. R. Nagarajan, L. Emmanuvel. Unusual Cleavage of N-N Bond of 1-Arylamino-1,2,3-triazole Derivatives: A Simple and Alternate Approach to 4,5-Disubstituted-1H-1,2,3-triazoles. Asian Journal of Chemistry 2019, 31 (5) , 1057-1061. https://doi.org/10.14233/ajchem.2019.21857
    28. James R. Walker, Jeffrey E. Merit, Rhiannon Thomas‐Tran, Doris T. Y. Tang, J. Du Bois. Divergent Synthesis of Natural Derivatives of (+)‐Saxitoxin Including 11‐Saxitoxinethanoic Acid. Angewandte Chemie 2019, 131 (6) , 1703-1707. https://doi.org/10.1002/ange.201811717
    29. James R. Walker, Jeffrey E. Merit, Rhiannon Thomas‐Tran, Doris T. Y. Tang, J. Du Bois. Divergent Synthesis of Natural Derivatives of (+)‐Saxitoxin Including 11‐Saxitoxinethanoic Acid. Angewandte Chemie International Edition 2019, 58 (6) , 1689-1693. https://doi.org/10.1002/anie.201811717
    30. Paolo Amabili, Adolfo Amici, Giovanni Campisi, Giulia Guerra, Magda Monari, Mario Orena, Fabio Piccinelli, Samuele Rinaldi, Alessandra Tolomelli. Synthesis of Enantiopure Isosteres of Amino Acids Containing a Quaternary Stereocenter: Experimental and Computational Evaluation of a Novel Class of Atropisomers. European Journal of Organic Chemistry 2018, 2018 (46) , 6524-6536. https://doi.org/10.1002/ejoc.201801213
    31. Yao Zhou, Qiuling Song. Oxidative ring-opening of 3-aminoindazoles for the synthesis of 2-aminobenzoates. Organic Chemistry Frontiers 2018, 5 (22) , 3245-3249. https://doi.org/10.1039/C8QO00872H
    32. Lorena M. Durán‐Riveroll, Allan D. Cembella, José Correa‐Basurto. Guanidinium Toxins: Natural Biogenic Origin, Chemistry, Biosynthesis, and Biotechnological Applications. 2018, 323-370. https://doi.org/10.1002/9783527801718.ch11
    33. Shigeki Tsuchiya, Yuko Cho, Renpei Yoshioka, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, Mari Yotsu‐Yamashita. Synthesis and Identification of Key Biosynthetic Intermediates for the Formation of the Tricyclic Skeleton of Saxitoxin. Angewandte Chemie 2017, 129 (19) , 5411-5415. https://doi.org/10.1002/ange.201612461
    34. Shigeki Tsuchiya, Yuko Cho, Renpei Yoshioka, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, Mari Yotsu‐Yamashita. Synthesis and Identification of Key Biosynthetic Intermediates for the Formation of the Tricyclic Skeleton of Saxitoxin. Angewandte Chemie International Edition 2017, 56 (19) , 5327-5331. https://doi.org/10.1002/anie.201612461
    35. André Shamsabadi, Jack Ren, Vijay Chudasama. Enabling the facile conversion of acyl hydrazides into N-acyl carbamates via metal-free ionic-based rupture of the N–N linkage. RSC Advances 2017, 7 (44) , 27608-27611. https://doi.org/10.1039/C7RA04178K
    36. Chao Wang, Mana Oki, Toru Nishikawa, Daisuke Harada, Mari Yotsu‐Yamashita, Kazuo Nagasawa. Total Synthesis of 11‐Saxitoxinethanoic Acid and Evaluation of its Inhibitory Activity on Voltage‐Gated Sodium Channels. Angewandte Chemie 2016, 128 (38) , 11772-11775. https://doi.org/10.1002/ange.201604155
    37. Chao Wang, Mana Oki, Toru Nishikawa, Daisuke Harada, Mari Yotsu‐Yamashita, Kazuo Nagasawa. Total Synthesis of 11‐Saxitoxinethanoic Acid and Evaluation of its Inhibitory Activity on Voltage‐Gated Sodium Channels. Angewandte Chemie International Edition 2016, 55 (38) , 11600-11603. https://doi.org/10.1002/anie.201604155
    38. Davide Romani, Shigeki Tsuchiya, Mari Yotsu-Yamashita, Silvia Antonia Brandán. Spectroscopic and structural investigation on intermediates species structurally associated to the tricyclic bisguanidine compound and to the toxic agent, saxitoxin. Journal of Molecular Structure 2016, 1119 , 25-38. https://doi.org/10.1016/j.molstruc.2016.04.039
    39. Shigeki Tsuchiya, Yuko Cho, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, Mari Yotsu-Yamashita. Biosynthetic route towards saxitoxin and shunt pathway. Scientific Reports 2016, 6 (1) https://doi.org/10.1038/srep20340
    40. Paolo Amabili, Adolfo Amici, Annafelicia Civitavecchia, Beatrice Maggiore, Mario Orena, Samuele Rinaldi, Alessandra Tolomelli. Highly stable atropisomers by electrophilic amination of a chiral γ-lactam within the synthesis of an elusive conformationally restricted analogue of α-methylhomoserine. Amino Acids 2016, 48 (2) , 461-478. https://doi.org/10.1007/s00726-015-2100-4
    41. Shigeki Tsuchiya, Yuko Cho, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, Mari Yotsu‐Yamashita. Synthesis of a Tricyclic Bisguanidine Compound Structurally Related to Saxitoxin and its Identification in Paralytic Shellfish Toxin‐Producing Microorganisms. Chemistry – A European Journal 2015, 21 (21) , 7835-7840. https://doi.org/10.1002/chem.201500064
    42. David A. Schiedler, Jessica K. Vellucci, Yi Lu, Christopher M. Beaudry. The development of carbon–carbon bond forming reactions of aminal radicals. Tetrahedron 2015, 71 (9) , 1448-1465. https://doi.org/10.1016/j.tet.2014.12.067
    43. Yuyong Ma, Saptarshi De, Chuo Chen. Syntheses of cyclic guanidine-containing natural products. Tetrahedron 2015, 71 (8) , 1145-1173. https://doi.org/10.1016/j.tet.2014.11.056
    44. Lyndon E. Llewellyn. Marine Biotoxins in History: Misuse and Mayhem. 2015, 571-588. https://doi.org/10.1007/978-94-007-5869-8_15
    45. René Pita, Arturo Anadón. Chemical Weapons of Mass Destruction and Terrorism. 2015, 55-65. https://doi.org/10.1016/B978-0-12-800159-2.00007-5
    46. Aaron D. Pearson, Robert M. Williams. Synthetic studies towards zetekitoxin AB: preparation of 4,5-epi-11-hydroxy-saxitoxinol. Tetrahedron 2014, 70 (43) , 7942-7949. https://doi.org/10.1016/j.tet.2014.08.058
    47. Jean‐Michel Kornprobst. Dinophyceae (Dinoflagellates). 2014, 1-50. https://doi.org/10.1002/9783527335855.marprod011
    48. Arun P. Thottumkara, William H. Parsons, J. Du Bois. Saxitoxin. Angewandte Chemie 2014, 126 (23) , 5868-5894. https://doi.org/10.1002/ange.201308235
    49. Arun P. Thottumkara, William H. Parsons, J. Du Bois. Saxitoxin. Angewandte Chemie International Edition 2014, 53 (23) , 5760-5784. https://doi.org/10.1002/anie.201308235
    50. Lyndon E. Llewellyn. Marine Biotoxins in History: Misuse and Mayhem. 2014, 1-16. https://doi.org/10.1007/978-94-007-6645-7_15-1
    51. Matthew G. Donahue. Recent Developments in the Synthesis of Cyclic Guanidine Alkaloids. 2014, 1-28. https://doi.org/10.1016/B978-0-08-100017-5.00001-7
    52. Julian Egger, Erick M. Carreira. Efficient synthesis strategies by application of transition metal-catalyzed carbene/nitrene insertions into C–H bonds. Nat. Prod. Rep. 2014, 31 (4) , 449-455. https://doi.org/10.1039/C3NP70084D
    53. Shigeki Tsuchiya, Yuko Cho, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, Mari Yotsu-Yamashita. Synthesis and identification of proposed biosynthetic intermediates of saxitoxin in the cyanobacterium Anabaena circinalis (TA04) and the dinoflagellate Alexandrium tamarense (Axat-2). Org. Biomol. Chem. 2014, 12 (19) , 3016-3020. https://doi.org/10.1039/C4OB00071D
    54. Ryuichi Sakai, Geoffrey T. Swanson. Recent progress in neuroactive marine natural products. Natural Product Reports 2014, 31 (2) , 273. https://doi.org/10.1039/c3np70083f
    55. . When Metathesis Fails. 2013, 201-224. https://doi.org/10.1002/9783527654628.ch9
    56. Ralf Kellmann, Olivier Ploux, Brett A. Neilan. Neurotoxic Alkaloids from Cyanobacteria. 2013, 39-83. https://doi.org/10.1007/978-3-642-22144-6_47
    57. Takafumi Akimoto, Asako Masuda, Mari Yotsu-Yamashita, Takatsugu Hirokawa, Kazuo Nagasawa. Synthesis of saxitoxin derivatives bearing guanidine and urea groups at C13 and evaluation of their inhibitory activity on voltage-gated sodium channels. Organic & Biomolecular Chemistry 2013, 11 (38) , 6642. https://doi.org/10.1039/c3ob41398e
    58. David Y.‐K. Chen, So Won Youn. CH Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products. Chemistry – A European Journal 2012, 18 (31) , 9452-9474. https://doi.org/10.1002/chem.201201329
    59. Hyukjae Choi, Alban R. Pereira, William H. Gerwick. The Chemistry of Marine Algae and Cyanobacteria. 2012, 55-152. https://doi.org/10.1007/978-90-481-3834-0_2
    60. J. Mulzer. 2.18 Selected Diastereoselective Reactions: Diastereoselective Intra- and Intermolecular 1,3-Dipolar Cycloadditions in Natural Product Synthesis. 2012, 525-562. https://doi.org/10.1016/B978-0-08-095167-6.00224-X
    61. Takuya Hashimoto, Hidenori Kimura, Yu Kawamata, Keiji Maruoka. Generation and exploitation of acyclic azomethine imines in chiral Brønsted acid catalysis. Nature Chemistry 2011, 3 (8) , 642-646. https://doi.org/10.1038/nchem.1096
    62. Yusuke Sawayama, Toshio Nishikawa. A Synthetic Route to the Saxitoxin Skeleton: Synthesis of Decarbamoyl α‐Saxitoxinol, an Analogue of Saxitoxin Produced by the Cyanobacterium Lyngbya wollei. Angewandte Chemie 2011, 123 (31) , 7314-7316. https://doi.org/10.1002/ange.201102494
    63. Yusuke Sawayama, Toshio Nishikawa. A Synthetic Route to the Saxitoxin Skeleton: Synthesis of Decarbamoyl α‐Saxitoxinol, an Analogue of Saxitoxin Produced by the Cyanobacterium Lyngbya wollei. Angewandte Chemie International Edition 2011, 50 (31) , 7176-7178. https://doi.org/10.1002/anie.201102494
    64. Zhao‐Quan He, Quan Zhou, Li Wu, Ying‐Chun Chen. Asymmetric Organocatalytic Tandem Reaction to Chiral Pyrimidinone Derivatives using Urea as Dinitrogen Source. Advanced Synthesis & Catalysis 2010, 352 (11-12) , 1904-1908. https://doi.org/10.1002/adsc.201000291
    65. Rómulo Aráoz, Jordi Molgó, Nicole Tandeau de Marsac. Neurotoxic cyanobacterial toxins. Toxicon 2010, 56 (5) , 813-828. https://doi.org/10.1016/j.toxicon.2009.07.036
    66. René Pita. Toxin weapons: from World War I to jihadi terrorism. Toxin Reviews 2009, 28 (4) , 219-237. https://doi.org/10.3109/15569540903246136
    67. Mahalingam Poornachandran, Raghavachary Raghunathan. Facile Synthesis of cis -Fused 1-Benzyl/- H -5-arylsulfonyl Pyrrolo[3,4- b ]pyrroles. Synthetic Communications 2009, 39 (5) , 917-926. https://doi.org/10.1080/00397910802440330
    68. Osamu Iwamoto, Ryoko Shinohara, Kazuo Nagasawa. Total Synthesis of (−)‐ and (+)‐Decarbamoyloxysaxitoxin and (+)‐Saxitoxin. Chemistry – An Asian Journal 2009, 4 (2) , 277-285. https://doi.org/10.1002/asia.200800382
    69. Daisuke Urabe. Total Syntheses of Saxitoxin and its Analogues. Journal of Synthetic Organic Chemistry, Japan 2009, 67 (3) , 248-249. https://doi.org/10.5059/yukigoseikyokaishi.67.248
    70. Mahalingam Poornachandran, Raghavachary Raghunathan. A novel diastereoselective 1,3-dipolar cycloaddition approach to cis-fused bispyrrolidines. Tetrahedron: Asymmetry 2008, 19 (18) , 2177-2183. https://doi.org/10.1016/j.tetasy.2008.09.007
    71. Mahalingam Poornachandran, Raghavachary Raghunathan. Synthesis of pyrrolo[3,4-b]pyrroles and perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles. Tetrahedron 2008, 64 (27) , 6461-6474. https://doi.org/10.1016/j.tet.2008.04.063
    72. Osamu Iwamoto, Hiroyuki Koshino, Daisuke Hashizume, Kazuo Nagasawa. Total Synthesis of (−)‐Decarbamoyloxysaxitoxin. Angewandte Chemie 2007, 119 (45) , 8779-8782. https://doi.org/10.1002/ange.200703326
    73. Osamu Iwamoto, Hiroyuki Koshino, Daisuke Hashizume, Kazuo Nagasawa. Total Synthesis of (−)‐Decarbamoyloxysaxitoxin. Angewandte Chemie International Edition 2007, 46 (45) , 8625-8628. https://doi.org/10.1002/anie.200703326
    74. Paul J. Dransfield, Anja S. Dilley, Shaohui Wang, Daniel Romo. A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal. Tetrahedron 2006, 62 (22) , 5223-5247. https://doi.org/10.1016/j.tet.2005.12.068
    75. Anne-Marie Sapse, Robert Rothchild, Kyu Rhee. An ab initio study of the guanidinium groups in saxitoxin. Journal of Molecular Modeling 2006, 12 (2) , 140-145. https://doi.org/10.1007/s00894-005-0005-y
    76. Lyndon E. Llewellyn. Saxitoxin, a toxic marine natural product that targets a multitude of receptors. Natural Product Reports 2006, 23 (2) , 200. https://doi.org/10.1039/b501296c
    77. Kazuo Nagasawa, Osamu Iwamoto, Miyuki Sekine, Hiroyuki Koshino. Regioselective Oxidation of Isoxazolidines to Ketonitrones. HETEROCYCLES 2006, 70 (1) , 107. https://doi.org/10.3987/COM-06-S(W)34
    78. Mahalingam Poornachandran, Raghavachary Raghunathan. A novel entry into 1-methyl- and 1-aryl-octahydropyrrolo[3,4-b]pyrroles and their N-1–C-2 fused derivatives: stereoselective synthesis via an intramolecular azomethine ylide cycloaddition reaction. Tetrahedron Letters 2005, 46 (42) , 7197-7200. https://doi.org/10.1016/j.tetlet.2005.08.077
    79. Florence Chung, Ariane Chauveau, Mohamed Seltki, Martine Bonin, Laurent Micouin. Asymmetric 1,3-dipolar cycloadditions of a chiral nonracemic glyoxylic azomethine imine. Tetrahedron Letters 2004, 45 (15) , 3127-3130. https://doi.org/10.1016/j.tetlet.2004.02.088
    80. Olivier Bedel, Dominique Urban, Yves Langlois. Oxazoline azomethine imines preparation and cycloaddition with phenyl isocyanate. Tetrahedron Letters 2002, 43 (4) , 607-609. https://doi.org/10.1016/S0040-4039(01)02244-4
    81. Eric D. Edstrom. Phenyl Chlorothionocarbonate. 2001https://doi.org/10.1002/047084289X.rp057
    82. Mark A Graham, Alan H Wadsworth, Mark Thornton-Pett, Benedetta Carrozzini, Giovanni L Cascarano, Christopher M Rayner. Mechanistic and stereochemical aspects of the Lewis acid mediated cleavage of α-aminoacetals. Tetrahedron Letters 2001, 42 (15) , 2865-2868. https://doi.org/10.1016/S0040-4039(01)00292-1
    83. K. C. Nicolaou, Dionisios Vourloumis, Nicolas Winssinger, Phil S. Baran. Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts. Angewandte Chemie 2000, 112 (1) , 46-126. https://doi.org/10.1002/(SICI)1521-3757(20000103)112:1<46::AID-ANGE46>3.0.CO;2-P
    84. Fanny Roussi, Martine Bonin, Angèle Chiaroni, Laurent Micouin, Claude Riche, Henri-Philippe Husson. Asymmetric 1,3-dipolar cycloadditions of a chiral non-racemic azomethine imine. Tetrahedron Letters 1999, 40 (19) , 3727-3730. https://doi.org/10.1016/S0040-4039(99)00610-3
    85. Quanying Liu, Allan P Marchington, Christopher M Rayner. Synthesis of new potential aminopeptidase inhibitors by Lewis acid induced rearrangement of 2,3-epoxy amines and regiospecific nucleophilic trapping of aziridinium ion intermediates with α-amino esters. Tetrahedron 1997, 53 (46) , 15729-15742. https://doi.org/10.1016/S0040-4020(97)00849-1
    86. Patrick J. Murphy, Williams Harri Lloyd, David E. Hibbs, Michael B. Hursthouse, K.M. Abdul Malik. Biomimetic model studies towards ptilomycalin A. Tetrahedron 1996, 52 (24) , 8315-8332. https://doi.org/10.1016/0040-4020(96)00385-7
    87. Vien V. Khau, Michael J. Martinelli. 1,3-Dipolar cycloreversion of a 1,3,4-oxadiazolidine as a controlled azomethine imine surrogate for pyrazolidine synthesis. Tetrahedron Letters 1996, 37 (25) , 4323-4326. https://doi.org/10.1016/0040-4039(96)00836-2
    88. Kyriacos Costa Nicolaou. The Total Synthesis of Brevetoxin B: A Twelve‐Year Odyssey in Organic Synthesis. Angewandte Chemie International Edition in English 1996, 35 (6) , 588-607. https://doi.org/10.1002/anie.199605881
    89. Kyriacos Costa Nicolaou. Die Totalsynthese von Brevetoxin B – eine zwölf Jahre währende Odyssee in der organischen Synthese. Angewandte Chemie 1996, 108 (6) , 644-664. https://doi.org/10.1002/ange.19961080605
    90. Roberto Gomes de Souza Berlinck. Some Aspects of Guanidine Secondary Metabolites. 1995, 119-295. https://doi.org/10.1007/978-3-7091-9363-1_2
    91. Maurice V. Laycock, Pierre Thibault, Stephen W. Ayer, John A. Walter. Isolation and purification procedures for the preparation of paralytic shellfish poisoning toxin standards. Natural Toxins 1994, 2 (4) , 175-183. https://doi.org/10.1002/nt.2620020405
    92. K. F. Albizati, V. A. Martin, M. R. Agharahimi, D. A. Stolze. References. 1992, 312-320. https://doi.org/10.1007/978-3-642-76838-5_6
    93. Peter A. Wade. Intramolecular 1,3-Dipolar Cycloadditions. 1991, 1111-1168. https://doi.org/10.1016/B978-0-08-052349-1.00117-7
    94. Peter A. Jacobi. The Total Synthesis of Saxitoxin. 1989, 191-219. https://doi.org/10.1016/B978-0-08-092429-8.50011-8
    95. Thomas L. Gilchrist, Deborah Hughes, Robert Wasson. Selective reduction and cleavage of the N-N bond of fused tetrahydropyridazines: a route to functionalised lactams. Tetrahedron Letters 1987, 28 (14) , 1573-1575. https://doi.org/10.1016/S0040-4039(01)81045-5
    96. P. A. JACOBI, M. J. MARTINELLI, S. POLANC. ChemInform Abstract: TOTAL SYNTHESIS OF (.+‐.)‐SAXITOXIN. Chemischer Informationsdienst 1985, 16 (2) https://doi.org/10.1002/chin.198502356
    97. Paul Armstrong, Ronald Grigg, Maurice W. Jordan, John F. Malone. X=y-zh systems as potential 1,3-dipoles—5. Tetrahedron 1985, 41 (17) , 3547-3558. https://doi.org/10.1016/S0040-4020(01)96708-0
    98. . Bioactive Marine Toxins. , 151-207. https://doi.org/10.1007/1-4020-3484-9_7
    99. Adam H Love. Determining important parameters related to cyanobacterial alkaloid toxin exposure. , 453-463. https://doi.org/10.1007/978-0-387-75865-7_18

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect