Structural Revision and Total Synthesis of Azaspiracid-1, Part 1: Intelligence Gathering and Tentative Proposal

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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  • 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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  • 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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  • 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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  • 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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  • David Y.-K. Chen 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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  • 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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  • 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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  • Yiwei Li 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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  • Masayuki Satake Prof. Dr.

    1. Graduate School of Agriculture, Tohoku University, Tsutsumi-dori Amamiya, Aoba-ku, Sendai 981-8555, Japan, Fax: (+81) 22-717-8817
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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 Japanese Society for the Advancement of Science (to Y.M.A.Y.), the National Science Foundation (to M.O.F.), and Eli Lilly (to Y.L.).

Abstract

original image

Phantommoleküle der Natur: Abbaustudien an Azaspiracid-1 (siehe die ursprünglich vorgeschlagene, falsche Struktur), dem berüchtigten Neurotoxin aus verunreinigten Muscheln, ergaben, dass die Doppelbindung im Ring A zwischen C7 und C8 vorliegt und nicht zwischen C8 und C9, und sie lieferten weitere Informationen zur generellen Stereochemie des Moleküls.

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