Synthesis of C-2 Taxol Analogues

Authors

  • Prof. Dr. Kyriacos Costa Nicolaou,

    Corresponding author
    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry, University of California, San Diego. 9500 Gilman Drive, La Jolla, CA 92093 (USA) Telefax: Int. code + (619)554-6738
    • Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA)
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  • Elias A. Couladouros,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry, University of California, San Diego. 9500 Gilman Drive, La Jolla, CA 92093 (USA) Telefax: Int. code + (619)554-6738
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  • Phillipe G. Nantermet,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry, University of California, San Diego. 9500 Gilman Drive, La Jolla, CA 92093 (USA) Telefax: Int. code + (619)554-6738
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  • Joanne Renaud,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry, University of California, San Diego. 9500 Gilman Drive, La Jolla, CA 92093 (USA) Telefax: Int. code + (619)554-6738
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  • Rodney Kiplin Guy,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry, University of California, San Diego. 9500 Gilman Drive, La Jolla, CA 92093 (USA) Telefax: Int. code + (619)554-6738
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  • Wolfgang Wrasidlo

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry, University of California, San Diego. 9500 Gilman Drive, La Jolla, CA 92093 (USA) Telefax: Int. code + (619)554-6738
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  • We thank E. Bombardelli for 10-deacetylbaccatin III, K. B. Sharpless for a series of diols, and I. Ojima for the β-lactam 6. This work was supported by The Scripps Research Institute, National Institutes of Health (USA), Office of Naval Research (USA) (R. K. G.), Natural Sciences and Engineering Research Council (Canada) (J. R.), the Agricultural University of Athens (E. A. C.), and Rhone-Poulenc Rorer (P. G. N.).

Abstract

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Nucleophilic ring opening of cyclic carbonates 1 leads regioselectively to the less substituted ester 2. Moreover, for molecules with several carbonyl groups the reaction is chemoselective: In a taxol precursor the carbonate group and not one of the three additional carbonyl groups was attacked; the resulting esters were converted into taxol analogues that displayed differing cytotoxicities.

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