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A Convergent Total Synthesis of Calicheamicin γmath image

Authors

  • Dr. Stephen A. Hitchcock,

    1. Department of Chemistry, Yale University, New Haven, CT 06511 (USA), Telefax: Int. code + (203)432-5098
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  • Serge H. Boyer,

    1. Department of Chemistry, Yale University, New Haven, CT 06511 (USA), Telefax: Int. code + (203)432-5098
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  • Margaret Y. Chu-Moyer,

    1. Department of Chemistry, Yale University, New Haven, CT 06511 (USA), Telefax: Int. code + (203)432-5098
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  • Steven H. Olson,

    1. Department of Chemistry, Yale University, New Haven, CT 06511 (USA), Telefax: Int. code + (203)432-5098
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  • Prof. Samuel J. Danishefsky

    Corresponding author
    1. Department of Chemistry, Yale University, New Haven, CT 06511 (USA), Telefax: Int. code + (203)432-5098
    Current affiliation:
    1. Memorial Sloan-Kettering Cancer Center 1275 York Avenue, New York, NY 10021 (USA), Telefax: Int. code + (212)772-8691 and Department of Chemistry, Havemeyer Hall Columbia University, New York, NY 10027 (USA), Telefax: Int. code + (212)854-7142
    • Department of Chemistry, Yale University, New Haven, CT 06511 (USA), Telefax: Int. code + (203)432-5098
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  • This research was supported by National Institutes of Health (Grant No. CA 28824). A NATO/SERC (Science and Engineering Research Council (UK)) Fellowship to S. A. H., a Kent Fellowship to S. H. B. and M. Y. C.-M., and an NSF Predoctoral Fellowship to M. Y. C.-M. are gratefully acknowledged.

Abstract

original image

Ultimate convergence for the total synthesis of calicheamicin γmath image has been achieved thanks to a remarkable glycosidation between the glycosyl donor 2 and aglycone ent-1 (see preceeding communication; R = SSMe, ketal-protected); after glycosidation the natural product is obtained in two steps.

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