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Divergent, generalized synthesis of unsymmetrically substituted 2,5-piperazinediones

Cite this: J. Am. Chem. Soc. 1985, 107, 11, 3246–3253
Publication Date (Print):May 1, 1985
https://doi.org/10.1021/ja00297a034
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    1. Travis C. McMahon, Sarah Stanley, Edward Kazyanskaya, Deborah Hung, and John L. Wood . The First Synthesis of an Epidiselenodiketopiperazine. Organic Letters 2012, 14 (17) , 4534-4536. https://doi.org/10.1021/ol3020094
    2. Alan D. Borthwick . 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products. Chemical Reviews 2012, 112 (7) , 3641-3716. https://doi.org/10.1021/cr200398y
    3. Robert M. Williams . Natural Products Synthesis: Enabling Tools To Penetrate Nature’s Secrets of Biogenesis and Biomechanism. The Journal of Organic Chemistry 2011, 76 (11) , 4221-4259. https://doi.org/10.1021/jo2003693
    4. Christopher J. Easton. Free-Radical Reactions in the Synthesis of α-Amino Acids and Derivatives. Chemical Reviews 1997, 97 (1) , 53-82. https://doi.org/10.1021/cr9402844
    5. Yingying Pan, Guodong Tang, Yilan Jiang, Linxia Jiang, Ju Zhang, Renjing Lu, Lance F. Culnane, Yu Zhang, Rongqing Li. Theoretical and experimental vibrational property of 1,3,4,6-tetramethylpiperazine-2,5-dione. Spectroscopy Letters 2016, 49 (10) , 647-653. https://doi.org/10.1080/00387010.2016.1240086
    6. Ren Takeuchi, Jun Shimokawa, Tohru Fukuyama. Development of a route to chiral epidithiodioxopiperazine moieties and application to the asymmetric synthesis of (+)-hyalodendrin. Chem. Sci. 2014, 5 (5) , 2003-2006. https://doi.org/10.1039/C3SC53222D
    7. Nigel S. Simpkins, Ilias Pavlakos, Michael D. Weller, Louise Male. The cascade radical cyclisation approach to prenylated alkaloids: synthesis of stephacidin A and notoamide B. Organic & Biomolecular Chemistry 2013, 11 (30) , 4957. https://doi.org/10.1039/c3ob40979a
    8. Nicolas Boyer, Karen C. Morrison, Justin Kim, Paul J. Hergenrother, Mohammad Movassaghi. Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids. Chemical Science 2013, 4 (4) , 1646. https://doi.org/10.1039/c3sc50174d
    9. Alexis Coste, Justin Kim, Timothy C. Adams, Mohammad Movassaghi. Concise total synthesis of (+)-bionectins A and C. Chemical Science 2013, 4 (8) , 3191. https://doi.org/10.1039/c3sc51150b
    10. Lihong Wang, Derrick L.J. Clive. Synthetic studies related to MPC1001: formation of a model epidithiodiketopiperazine. Tetrahedron Letters 2012, 53 (12) , 1504-1506. https://doi.org/10.1016/j.tetlet.2012.01.055
    11. Nicolas Boyer, Mohammad Movassaghi. Concise total synthesis of (+)-gliocladins B and C. Chemical Science 2012, 3 (6) , 1798. https://doi.org/10.1039/c2sc20270k
    12. Eriko Iwasa, Yoshitaka Hamashima, Shinya Fujishiro, Daisuke Hashizume, Mikiko Sodeoka. Total syntheses of chaetocin and ent-chaetocin. Tetrahedron 2011, 67 (35) , 6587-6599. https://doi.org/10.1016/j.tet.2011.05.081
    13. Frédéric C. Frebault, Nigel S. Simpkins. A cationic cyclisation route to prenylated indole alkaloids: synthesis of malbrancheamide B and brevianamide B, and progress towards stephacidin A. Tetrahedron 2010, 66 (33) , 6585-6596. https://doi.org/10.1016/j.tet.2010.04.093
    14. Mark Pichowicz, Nigel S. Simpkins, Alexander J. Blake, Claire Wilson. Studies towards complex bridged alkaloids: regio- and stereocontrolled enolate chemistry of 2,5-diketopiperazines. Tetrahedron 2008, 64 (17) , 3713-3735. https://doi.org/10.1016/j.tet.2008.02.020
    15. Edward J. Adams, Troels Skrydstrup, Karl B. Lindsay, Troels Skrydstrup, Karl B. Lindsay. 2-Pyridinethiol. 2007https://doi.org/10.1002/047084289X.rp286.pub3
    16. Mark Pichowicz, Nigel S. Simpkins, Alexander J. Blake, Claire Wilson. Synthesis towards complex bridged alkaloids derived from diketopiperazines: a cationic cascade approach to stephacidins, paraherquamides and related systems. Tetrahedron Letters 2006, 47 (47) , 8413-8417. https://doi.org/10.1016/j.tetlet.2006.09.046
    17. Steven D. Bull, Stephen G. Davies, A. Christopher Garner, Edward D. Savory, Emma J. Snow, Andrew D. Smith. 2-Halo-diketopiperazines as chiral glycine cation equivalents. Tetrahedron: Asymmetry 2004, 15 (24) , 3989-4001. https://doi.org/10.1016/j.tetasy.2004.11.022
    18. Rick Attrill, Heather Tye, Liam R Cox. α-Amino acid synthesis via a Cu(II) chiral Lewis acid mediated addition of soft carbon nucleophiles to glycine cation equivalents. Tetrahedron: Asymmetry 2004, 15 (11) , 1681-1684. https://doi.org/10.1016/j.tetasy.2004.04.018
    19. Cécile Vanier, Alain Wagner, Charles Mioskowski. Preparation of Resin-BoundN-(α-Methoxyalkyl)amides: An Advantageous Use of Solid-Phase Chemistry for the Handling of Unstable Precursors of the VersatileN-Acyliminium Ions. Chemistry 2001, 7 (11) , 2318-2323. https://doi.org/10.1002/1521-3765(20010601)7:11<2318::AID-CHEM23180>3.0.CO;2-W
    20. Christopher J. Easton. Modifications of Amino Acids and Peptides via Radicals. 2001, 505-522. https://doi.org/10.1002/9783527618293.ch50
    21. Marı́a Luisa Heredia, Marı́a Fernández, Elena de la Cuesta, Carmen Avendaño. 1-Bromo-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones as α-bromoglycine templates. Tetrahedron: Asymmetry 2001, 12 (3) , 411-418. https://doi.org/10.1016/S0957-4166(01)00067-2
    22. Xiaolun Wang, Xu Chen, Hongzhen Lian, Yi Pan, Yaozeng Shi. Syntheses Of Ketene Dithioacetal Derivatives Of 2,5-Piperazinedione. Synthetic Communications 1999, 29 (9) , 1553-1560. https://doi.org/10.1080/00397919908086135
    23. Saskia Louwrier, Martin Ostendorf, Arnoud Boom, Henk Hiemstra, W. Nico Speckamp. Studies towards the synthesis of (+)-ptilomycalin A; Stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams. Tetrahedron 1996, 52 (7) , 2603-2628. https://doi.org/10.1016/0040-4020(95)01085-8
    24. Robert M. Williams. Asymmetric syntheses of α-amino acids. 1995, 45-94. https://doi.org/10.1016/S1874-5148(06)80005-9
    25. Patrick D. Bailey, Joanne Clayson, Andrew N. Boa. α-Cation equivalents of amino acids. Contemp. Org. Synth. 1995, 2 (3) , 173-187. https://doi.org/10.1039/CO9950200173
    26. Robert M. Williams. Stereoselective Synthetic and Mechanistic Chemistry of Bicyclomycin. 1993, 63-112. https://doi.org/10.1016/B978-0-444-89366-6.70009-5
    27. Srinivasachari Rajappa, Mandakini Vishvanath Natekar. Piperazine-2,5-diones and Related Lactim Ethers. 1993, 187-289. https://doi.org/10.1016/S0065-2725(08)60889-2
    28. Harry H. Wasserman, Vincent M. Rotello, Giuseppina B. Krause. Oxidation of α-ylido, β-keto amides to vicinal tricarbonyls. Synthesis of a diketopiperazine precursor of bicyclomycin.. Tetrahedron Letters 1992, 33 (37) , 5419-5422. https://doi.org/10.1016/S0040-4039(00)79110-6
    29. Dearg S. Brown, Philippe Charreau, Thomas Hansson, Steven V. Ley. Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone. Tetrahedron 1991, 47 (7) , 1311-1328. https://doi.org/10.1016/S0040-4020(01)86388-2
    30. R. M. WILLIAMS, R. W. ARMSTRONG, L. K. MARUYAMA, J.‐S. DUNG, O. P. ANDERSON. ChemInform Abstract: DIVERGENT, GENERALIZED SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED 2,5‐PIPERAZINEDIONES. Chemischer Informationsdienst 1985, 16 (38) https://doi.org/10.1002/chin.198538239
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