Get access
Advertisement

Total Synthesis of Sporolide B

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)
    Search for more papers by this author
  • Yefeng Tang 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)
    Search for more papers by this author
  • Jianhua Wang

    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)
    Search for more papers by this author

  • We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectroscopic assistance, respectively. We thank Dr. R. Hungate and R. Jensen of Amgen, Thousand Oaks, California, for the 13C NMR spectrum of synthetic sporolide B and Prof. W. Fenical for a sample of natural sporolide B. Financial support for this work was provided by the National Institutes of Health (USA), the Skaggs Institute for Research, and an Andrea Elizabeth Vogt Memorial Fellowship (to J.W.).

Abstract

Aus dem Meer gefischt: Die erste Totalsynthese des hoch oxygenierten marinen Naturstoffs Sporolid B gelang mithilfe einer konvergenten Strategie. Als Schlüsselschritte sind eine rutheniumkatalysierte [2+2+2]-Cycloaddition, die das Indensystem aufbaut, und eine thermische Diels-Alder-Reaktion beim Ringschluss zum Makrocyclus hervorzuheben (siehe Schema).

original image
Get access to the full text of this article

Ancillary