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Total Synthesis of (+)-Rugulosin and (+)-2,2′-epi-Cytoskyrin A through Cascade Reactions

Authors

  • K. C. Nicolaou Prof. Dr.,

    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, Fax: (+1) 858-784-2469
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
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  • Yee Hwee Lim,

    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, Fax: (+1) 858-784-2469
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
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  • Charles D. Papageorgiou Dr.,

    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, Fax: (+1) 858-784-2469
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
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  • Jared L. Piper Dr.

    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, Fax: (+1) 858-784-2469
    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 Dr. D. H. Huang, Dr. G. Siuzdak, and Dr. R. K. Chadha for NMR spectroscopic, mass spectrometric, and X-ray crystallographic 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, a predoctoral fellowship from the A*STAR NSS Overseas PhD Scholarship (to Y.H.L.), and a postdoctoral fellowship from the George E. Hewitt Foundation (to J.L.P.).

Abstract

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Die Cytoskyrin-Kaskade: Die Totalsynthesen der Bisanthrachinone 2 (+)-2,2′-epi-Cytoskyrin A (R2=OMe) und (+)-Rugulosin (R2=Me) gelang mithilfe einer Kaskadensequenz ausgehend von monomeren Anthradihydrochinoneinheiten 1.

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