Get access
Advertisement

Cascade Reactions Involving Formal [2+2] Thermal Cycloadditions: Total Synthesis of Artochamins F, H, I, and J

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
  • Troy Lister 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
  • Ross M. Denton 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
  • Christine F. Gelin

    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 wish to thank Dr. D. H. Huang, Dr. G. Siuzdak, and Dr. R. J. Chadha for assistance with NMR spectroscopy, mass spectrometry, and X-ray crystallography, respectively. Financial support for this work was provided by grants from the National Institutes of Health (USA) and the National Science Foundation (No. 06032187), the Skaggs Institute for Chemical Biology, and a National Science Foundation predoctoral fellowship (to C.F.G.).

Abstract

original image

Flexibel zum Erfolg: Die Totalsynthesen der Artochamine F (1), H (2), I (3) und J (4; siehe Schema) gelangen mithilfe einer flexiblen Strategie, zu der eine Kaskadensequenz aus zwei simultanen [3,3]-sigmatropen Umlagerungen und einer ungewöhnlichen intramolekularen thermischen [2+2]-Cycloaddition zwischen einem elektronenreichen Stilben und einer Prenylgruppe gehört.

Get access to the full text of this article

Ancillary