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Structural Revision and Total Synthesis of Azaspiracid-1, Part 2: Definition of the ABCD Domain and Total Synthesis

Authors

  • K. C. Nicolaou Prof. Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • Theocharis V. Koftis Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • Stepan Vyskocil Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • Goran Petrovic Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • Taotao Ling Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • Yoichi M. A. Yamada Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • Wenjun Tang Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • Michael O. Frederick

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, CA 92 037, USA, Fax: (+1) 858-784-2469 and, Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92 093, USA
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  • We thank Dr. D. H. Huang and Dr. G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. Financial support for this work was provided by grants from the National Institutes of Health (USA) and the Skaggs Institute for Chemical Biology, and fellowships from the Ernst Schering AG Foundation (to S.V.), the National Science Foundation (to M.O.F.), and the Japanese Society for the Advancement of Science (to Y.M.A.Y.).

Abstract

original image

Die Jagd auf die Struktur von Azaspiracid-1 ging mit einer revidierten Struktur (siehe Bild) zu Ende. Die Totalsynthese dieser anspruchsvollen Zielverbindung hat ein weiteres Kapitel in einer spannenden chemischen Detektivgeschichte abgeschlossen und die Bestimmung von relativer wie absoluter Konfiguration des Moleküls ermöglicht.

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