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A Practical Sulfenylation of 2,5-Diketopiperazines

Authors

  • Prof. Dr. K. C. Nicolaou,

    Corresponding author
    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
    • Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
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  • Dr. Denis Giguère,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Sotirios Totokotsopoulos,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Dr. Ya-Ping Sun

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • We thank Drs. D. H. Huang and L. Pasternack for NMR spectroscopic assistance, Dr. R. Chadha for X-ray crystallographic assistance and Dr. G. Siuzdak for mass spectrometric assistance. This work was supported by the Skaggs Institute for Research and grants from the National Institutes of Health (USA) and National Science Foundation (USA), as well as a postdoctoral fellowship from Fonds de Recherche Québec (to D.G.).

Abstract

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Schwefel in Aktion: Eine praktische und einfache Methode zur Einführung von Schwefelatomen in 2,5-Diketopiperazine (I) unter milden Bedingungen wurde entwickelt. Die Reaktion liefert Epidithiodiketopiperazine (II) und Bismethylthiodiketopiperazine (III) verschiedenster Komplexität.

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