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Total Synthesis and Structural Revision of (+)-Cristatumin C

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Departamento de Química Orgánica, Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Spain
*Tel: +34-986-812316. Fax: +34-986-818622. E-mail: [email protected] (Á. de Lera).
Cite this: J. Nat. Prod. 2014, 77, 2, 421–423
Publication Date (Web):January 17, 2014
Copyright © 2014 The American Chemical Society and American Society of Pharmacognosy

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    Abstract Image

    Naturally occurring (+)-cristatumin C, a bis-pyrrolidinoindoline diketopiperazine alkaloid isolated from Eurotium cristatum EN-220, is the 2R,3R,11S,15R,2′R,3′R,11′S,15′S enantiomer, as confirmed by total synthesis.

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    Comparison of the NMR data of natural and synthetic cristatumin C, spectroscopic data for homodimers 12 and 13, and copies of 1H NMR and 13C NMR spectra. This material is available free of charge via the Internet at

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    Cited By

    This article is cited by 17 publications.

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    5. Katherine L. Walker, Richard P. Loach, Mohammad Movassaghi. Total synthesis of complex 2,5-diketopiperazine alkaloids. 2023, 159-206.
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    8. Patricia García-Domínguez, Andrea Areal, Rosana Alvarez, Angel R. de Lera. Chemical synthesis in competition with global genome mining and heterologous expression for the preparation of dimeric tryptophan-derived 2,5-dioxopiperazines. Natural Product Reports 2022, 39 (6) , 1172-1225.
    9. Zhixian Ma, Ankun Zhou, Chengfeng Xia. Strategies for total synthesis of bispyrrolidinoindoline alkaloids. Natural Product Reports 2022, 39 (5) , 1015-1044.
    10. José A. Souto, David Román, Marta Domínguez, Ángel R. de Lera. Synthetic Studies on Alotamide A: Construction of N ‐Demethylalotamide A. European Journal of Organic Chemistry 2021, 2021 (44) , 6057-6070.
    11. Nelson G. M. Gomes, Renato B. Pereira, Paula B. Andrade, Patrícia Valentão. Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers. Marine Drugs 2019, 17 (10) , 551.
    12. Iago Alonso, Rosana Alvarez, Ángel R. de Lera. Indole–Indole Ullmann Cross‐Coupling for C Ar –N Bond Formation: Total Synthesis of (–)‐Aspergilazine A. European Journal of Organic Chemistry 2017, 2017 (33) , 4948-4954.
    13. Kangjiang Liang, Chengfeng Xia. Recent Advances of Transition Metal‐Mediated Oxidative Radical Reactions in Total Synthesis of Indole Alkaloids. Chinese Journal of Chemistry 2017, 35 (3) , 255-270.
    14. Nai-Yun Ji, Bin-Gui Wang. Mycochemistry of marine algicolous fungi. Fungal Diversity 2016, 80 (1) , 301-342.
    15. Shinji Tadano, Yukihiro Sugimachi, Michinori Sumimoto, Sachiko Tsukamoto, Hayato Ishikawa. Collective Synthesis and Biological Evaluation of Tryptophan‐Based Dimeric Diketopiperazine Alkaloids. Chemistry – A European Journal 2016, 22 (4) , 1277-1291.
    16. John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, Michèle R. Prinsep. Marine natural products. Natural Product Reports 2016, 33 (3) , 382-431.
    17. Hayato Ishikawa. Unified Total Synthesis of Tryptophan-based Dimeric Diketopiperazine Alkaloids. Journal of Synthetic Organic Chemistry, Japan 2016, 74 (2) , 104-116.

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