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An Expedient Synthesis of a Functionalized Core Structure of Bielschowskysin

Authors

  • Prof. Dr. K. C. Nicolaou,

    Corresponding author
    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)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA), Fax: (+1) 858-784-2469
    • Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
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  • Dr. Vikrant A. Adsool,

    1. Chemical Synthesis Laboratory@Biopolis, Agency for Science, Technology, and Research (A*STAR), Singapore 138667 (Singapore)
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  • Christopher R. H. Hale

    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)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA), Fax: (+1) 858-784-2469
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  • We thank Dr. D.-H. Huang and Dr. R. Chadha for spectroscopic and X-ray crystallographic assistance, respectively, and Dr. G. Siuzdak and Doris Tan for mass spectrometric assistance. Financial support for this work was provided by A*STAR, Singapore, the Skaggs Institute for Chemical Research, the National Institutes of Health (grant AI 055475-09), and the National Science Foundation (Graduate Research Fellowship to C.R.H.H.).

Abstract

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Photons in action: Cascade sequences, brevity, and efficiency are the hallmarks of the synthesis of a functionalized tricyclo[9.3.0.0]tetradecane ring system of the marine natural product bielschowskysin. The synthesis is achieved in five steps, with the key step being an exquisite intramolecular [2+2] photocycloaddition of a macrocyclic precursor (see scheme).

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